WO2007035066A1 - Procédé de fabrication de 3-acyloxy-gamma-butyrolactone optiquement actif et de 3-hydroxy-gamma-butyrolactone optiquement actif par procédé enzymatique - Google Patents
Procédé de fabrication de 3-acyloxy-gamma-butyrolactone optiquement actif et de 3-hydroxy-gamma-butyrolactone optiquement actif par procédé enzymatique Download PDFInfo
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- WO2007035066A1 WO2007035066A1 PCT/KR2006/003799 KR2006003799W WO2007035066A1 WO 2007035066 A1 WO2007035066 A1 WO 2007035066A1 KR 2006003799 W KR2006003799 W KR 2006003799W WO 2007035066 A1 WO2007035066 A1 WO 2007035066A1
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- WO
- WIPO (PCT)
- Prior art keywords
- gamma
- butyrolactone
- acyloxy
- optically active
- racemic
- Prior art date
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- FUDDLSHBRSNCBV-UHFFFAOYSA-N 4-hydroxyoxolan-2-one Chemical compound OC1COC(=O)C1 FUDDLSHBRSNCBV-UHFFFAOYSA-N 0.000 title claims abstract description 42
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 9
- 238000006911 enzymatic reaction Methods 0.000 title abstract description 4
- 238000000034 method Methods 0.000 claims abstract description 22
- 108090001060 Lipase Proteins 0.000 claims abstract description 10
- 239000004367 Lipase Substances 0.000 claims abstract description 10
- 102000004882 Lipase Human genes 0.000 claims abstract description 10
- 235000019421 lipase Nutrition 0.000 claims abstract description 10
- 244000005700 microbiome Species 0.000 claims abstract description 10
- 230000003287 optical effect Effects 0.000 claims abstract description 6
- LHBPNZDUNCZWFL-UHFFFAOYSA-N 4-chloro-3-hydroxybutanenitrile Chemical compound ClCC(O)CC#N LHBPNZDUNCZWFL-UHFFFAOYSA-N 0.000 claims abstract description 5
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000012074 organic phase Substances 0.000 claims abstract 2
- 239000012071 phase Substances 0.000 claims abstract 2
- 108090000790 Enzymes Proteins 0.000 claims description 8
- 102000004190 Enzymes Human genes 0.000 claims description 8
- 230000007062 hydrolysis Effects 0.000 claims description 5
- 238000006460 hydrolysis reaction Methods 0.000 claims description 5
- 239000011942 biocatalyst Substances 0.000 claims description 2
- 108090000371 Esterases Proteins 0.000 claims 1
- 108091005804 Peptidases Proteins 0.000 claims 1
- 239000004365 Protease Substances 0.000 claims 1
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 11
- FUDDLSHBRSNCBV-VKHMYHEASA-N (4s)-4-hydroxyoxolan-2-one Chemical compound O[C@@H]1COC(=O)C1 FUDDLSHBRSNCBV-VKHMYHEASA-N 0.000 description 9
- HCBUCWBBESELHL-UHFFFAOYSA-N 4-butoxyoxolan-2-one Chemical compound CCCCOC1COC(=O)C1 HCBUCWBBESELHL-UHFFFAOYSA-N 0.000 description 7
- QOAAHMCFVNHTBI-UHFFFAOYSA-N (5-oxooxolan-3-yl) acetate Chemical compound CC(=O)OC1COC(=O)C1 QOAAHMCFVNHTBI-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- ZAJNMXDBJKCCAT-UHFFFAOYSA-N ethyl 4-chloro-3-hydroxybutanoate Chemical compound CCOC(=O)CC(O)CCl ZAJNMXDBJKCCAT-UHFFFAOYSA-N 0.000 description 3
- 235000011090 malic acid Nutrition 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- BRLQWZUYTZBJKN-GSVOUGTGSA-N (+)-Epichlorohydrin Chemical compound ClC[C@@H]1CO1 BRLQWZUYTZBJKN-GSVOUGTGSA-N 0.000 description 2
- LHBPNZDUNCZWFL-BYPYZUCNSA-N (3s)-4-chloro-3-hydroxybutanenitrile Chemical compound ClC[C@@H](O)CC#N LHBPNZDUNCZWFL-BYPYZUCNSA-N 0.000 description 2
- HCBUCWBBESELHL-SSDOTTSWSA-N (4r)-4-butoxyoxolan-2-one Chemical compound CCCCO[C@H]1COC(=O)C1 HCBUCWBBESELHL-SSDOTTSWSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- QOAAHMCFVNHTBI-RXMQYKEDSA-N [(3r)-5-oxooxolan-3-yl] acetate Chemical compound CC(=O)O[C@H]1COC(=O)C1 QOAAHMCFVNHTBI-RXMQYKEDSA-N 0.000 description 2
- QOAAHMCFVNHTBI-YFKPBYRVSA-N [(3s)-5-oxooxolan-3-yl] acetate Chemical compound CC(=O)O[C@@H]1COC(=O)C1 QOAAHMCFVNHTBI-YFKPBYRVSA-N 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 230000020176 deacylation Effects 0.000 description 2
- 238000005947 deacylation reaction Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 229940099690 malic acid Drugs 0.000 description 2
- 239000001630 malic acid Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- SNZQJSZZDOZNGW-UHFFFAOYSA-N (2-oxooxolan-3-yl) acetate Chemical compound CC(=O)OC1CCOC1=O SNZQJSZZDOZNGW-UHFFFAOYSA-N 0.000 description 1
- UYVRPHIVOKUAPF-BYPYZUCNSA-N (2s)-2-acetyloxybutanedioic acid Chemical compound CC(=O)O[C@H](C(O)=O)CC(O)=O UYVRPHIVOKUAPF-BYPYZUCNSA-N 0.000 description 1
- FUDDLSHBRSNCBV-GSVOUGTGSA-N (4r)-4-hydroxyoxolan-2-one Chemical compound O[C@H]1COC(=O)C1 FUDDLSHBRSNCBV-GSVOUGTGSA-N 0.000 description 1
- HCBUCWBBESELHL-ZETCQYMHSA-N (4s)-4-butoxyoxolan-2-one Chemical compound CCCCO[C@@H]1COC(=O)C1 HCBUCWBBESELHL-ZETCQYMHSA-N 0.000 description 1
- PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical compound C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 description 1
- DZAIOXUZHHTJKN-VKHMYHEASA-N 3S,4-dihydroxy-butyric acid Chemical compound OC[C@@H](O)CC(O)=O DZAIOXUZHHTJKN-VKHMYHEASA-N 0.000 description 1
- -1 CAL B(Novozym 435 Chemical class 0.000 description 1
- 208000031226 Hyperlipidaemia Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- 108010084311 Novozyme 435 Proteins 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- FYGDTMLNYKFZSV-DZOUCCHMSA-N alpha-D-Glcp-(1->4)-alpha-D-Glcp-(1->4)-D-Glcp Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)O[C@H](O[C@@H]2[C@H](OC(O)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O FYGDTMLNYKFZSV-DZOUCCHMSA-N 0.000 description 1
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007071 enzymatic hydrolysis Effects 0.000 description 1
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 description 1
- OHLRLMWUFVDREV-UHFFFAOYSA-N ethyl 4-chloro-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)CCl OHLRLMWUFVDREV-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229940116298 l- malic acid Drugs 0.000 description 1
- FNDIBEBXSSGTIM-UHFFFAOYSA-N methyl 2,2-dihydroxybutanoate Chemical compound CCC(O)(O)C(=O)OC FNDIBEBXSSGTIM-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012450 pharmaceutical intermediate Substances 0.000 description 1
- 239000008057 potassium phosphate buffer Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
Definitions
- the present invention relates to process for the preparation of optically active
- 3-acyloxy-gamma-butyrolactone repesented by the general formula 5 and optically active 3-hydroxy-gamma-butyrolactone represented by the general formula 6 in scheme 1 from racemic 3-acyloxy-gamma-butyrolactone by enzymatic method.
- racemic 4-chloro-3-hydroxybutyronitrile(2), racemic 3-hydroxy-gamma-butyrolactone(3), racemic 3-acyloxy-gamma-butyrolactone (4) is prepared from racemic epichlorohydrin(l) in turn, racemic
- 3-acyloxy-gamma-butyrolactone is hydrolyzed stereospecifically by lipases or lipase- producing microorganisms in aqeous phase or organic Dphase containing water for the preparation of optically active 3-hydroxy-gamma-butyrolactone and optically active 3-acyloxy-gamma-butyrolactone.
- Optically active 3-acyloxy-gamma-butyrolactone can be converted to optically active 3-hydroxy-gamma-butyrolactone by deacylation, and is used for precursor of other useful substances. According to this invention, it is possible to transform 3-acyloxy-gamma-butyrolactone with low optical purity into 3-acyloxy-gamma-butyrolactone or 3-hydroxy-gamma-butyrolactone with high optical purity.
- 3-acyloxy-gamma-butyrolactone are important intermediates. Particularly they are used in preparing pharmaceuticals such as L-carnitine, hypertension drug and hyper- lipidemia drug.
- Daicel, Ltd. produced optically active 3-hydroxy-gamma-butyrolactone(93.9%e.e) from optically active ethyl 4-chloro-3-hydroxybutyrate using microorganism, but this method is not useful for industrial use because substrate concentration is low(JP 2002-204699). And in the same way, they produced optically active 3-hydroxy-gamma-butyrolactone from racemic ethyl 4-chloro-3-hydroxybutyrate, but they obtained the compound with low optical purity.
- the present invention relates to process for the preparation of optically active
- this invention includes the process for preparing 3-hydroxy-gamma-butyrolactone from epichlorohydrin one by one, and 3-acyloxy-gamma-butyrolactone is obtained by acylation. Racemic 3-acyloxy-gamma-butyrolactone is subjected to produce optically active 3-acyloxy-gamma-butyrolactone and optically active
- lipases such as CAL B(Novozym 435,
- Racemic 3-hydroxy-gamma-butyrolactone is determined using HP-FFAP column(Agilent, Inc., 3O m X 0.53 mm). The oven temperature was maintained initially at 100 0 C for 5 min and then raised at the rate of 20 °C/min to 220 0 C, and maintained for 10 min. Helium gas was used as carrier and compounds were detected using FID at 220 0 C. In this condition the typical retention time of the compounds was as follows:
- 3-acyloxy-gamma-butyrolactone were determined by HPLC(LAB Alliance, Model 201) equipped with chiral column AD-H(Daicel, 0.46 cm X 25 cm). Hexane and isopropyl alcohol mixture(90:10) used as mobile phase and flow rate was 0.7 ml/min, and the absorbance was 220nm.
- the typical retention time of the compounds in this invention was as follows:
- Example 1 Preparing of racemic 3-acetoxy-gamma-butyrolactone [37] [38] Pyridine(1.8 g) and acetyl chloride(1.57 g) was added to 20 ml of chloroform containing racemic 3-hydroxy-gamma-butyrolactone at 0 0 C and stirred at room temperature for 2 hours. The reaction mixture was extracted with organic solvent and concentrated to afford 1.83 g of racemic 3-acetoxy-gamma-butyrolactone. And this compound was confirmed by nuclear magnetic resonance.
- Example 2 Hydrolysis of racemic 3-acetoxy-gamma-butyrolactone
- Example 3 Racemic 3-acetoxy-gamma-butyrolactone(5%(v/v)) prepared from Example 1 was added to 4.75 ml 0.2 M potassium phosphate buffer(pH 7.0) and the reaction was carried out at 30 0 C after adding lipase CAL B. The reaction mixture was extracted with ethyl acetate and (R)-3-acetoxy-gamma-butyrolactone and (S)-3-hydroxy-gamma-butyrolactone was analyzed by above-mentioned method. The results are shown in Table 1.
- Example 3 Preparation of racemic 3-butoxy-gamma-butyrolactone [47] [48] Pyridine(3.5g) and butyryl chloride(4.7 g) was added to 100 ml of chloroform containing racemic 3-hydroxy-gamma-butyrolactone at 0 0 C and stirred at room temperature. The reaction mixture was extracted with organic solvent and concentrated to afford racemic 3-butoxy-gamma-butyrolactone. And this compound was confirmed by nuclear magnetic resonance.
- racemic 3-acyloxy-gamma-butyrolactone is hydrolyzed to optically active 3-acyloxy-gamma-butyrolactone and optically active 3-hydroxy-gamma-butyrolactone, also it is easy to seperate products from reaction mixture.
- Optically active 3-acyloxy-gamma-butyrolactone produced according to this invention can be converted to optically active 3-hydroxy-gamma-butyrolactone by deacylation. Therefore, this method is an useful process on the industrial scale for making optically active 3-acyloxy-gamma-butyrolactone or optically active 3-hydroxy-gamma-butyrolactone used as pharmaceutical intermediates.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
La présente invention concerne le procédé de préparation par procédé enzymatique de 3-acyloxy-gamma-butyrolactone optiquement actif représenté par la formule générale 5 et de 3-hydroxy-gamma-butyrolactone optiquement actif représenté par la formule générale 6 dans le schéma 1 à partir de 3-acyloxy-gamma-butyrolactone racémique optiquement actif représenté par la formule générale 4. Plus précisément, la présente invention concerne le procédé de préparation de 3-acyloxy-gamma-butyrolactone optiquement actif et de 3-hydroxy-gamma-butyrolactone optiquement actif où de l’épichlorohydrine représentée par la formule générale 1 est soumise à la production de 4-chloro-3-hydroxybutyronitrile racémique, de 3-hydroxy-gamma-butyrolactone racémique et de 3-acyloxy-gamma-butyrolactone racémique à tour de rôle et où l’on hydrolyse stérospécifiquement le 3-acyloxy-gamma-butyrolactone à l’aide de lipases ou de microorganismes producteurs de lipase en phase aqueuse ou en phase organique contenant de l’eau. Ce procédé est utile dans le procédé pratique car la production et la séparation de composés avec une grande pureté optique sont plus faciles qu’avec les autres procédés ayant fait l’objet d’un rapport.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR20050089119 | 2005-09-26 | ||
| KR10-2005-0089119 | 2005-09-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2007035066A1 true WO2007035066A1 (fr) | 2007-03-29 |
Family
ID=37889072
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/KR2006/003799 WO2007035066A1 (fr) | 2005-09-26 | 2006-09-25 | Procédé de fabrication de 3-acyloxy-gamma-butyrolactone optiquement actif et de 3-hydroxy-gamma-butyrolactone optiquement actif par procédé enzymatique |
Country Status (1)
| Country | Link |
|---|---|
| WO (1) | WO2007035066A1 (fr) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5084392A (en) * | 1990-02-02 | 1992-01-28 | Chisso Corporation | Process for producing optically active hydroxy lactones |
| JP2002204699A (ja) * | 2001-01-11 | 2002-07-23 | Daicel Chem Ind Ltd | β−ヒドロキシ−γ−ブチロラクトンの製造方法 |
-
2006
- 2006-09-25 WO PCT/KR2006/003799 patent/WO2007035066A1/fr active Application Filing
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5084392A (en) * | 1990-02-02 | 1992-01-28 | Chisso Corporation | Process for producing optically active hydroxy lactones |
| JP2002204699A (ja) * | 2001-01-11 | 2002-07-23 | Daicel Chem Ind Ltd | β−ヒドロキシ−γ−ブチロラクトンの製造方法 |
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