JPH01309696A - 光学活性オキサゾリジノン誘導体の製造方法 - Google Patents
光学活性オキサゾリジノン誘導体の製造方法Info
- Publication number
- JPH01309696A JPH01309696A JP10193989A JP10193989A JPH01309696A JP H01309696 A JPH01309696 A JP H01309696A JP 10193989 A JP10193989 A JP 10193989A JP 10193989 A JP10193989 A JP 10193989A JP H01309696 A JPH01309696 A JP H01309696A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- substituted
- formula
- group
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 25
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical class O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 85
- 108090000790 Enzymes Proteins 0.000 claims abstract description 50
- 102000004190 Enzymes Human genes 0.000 claims abstract description 50
- 210000004185 liver Anatomy 0.000 claims abstract description 19
- 108090000371 Esterases Proteins 0.000 claims abstract description 13
- 239000000126 substance Substances 0.000 claims abstract description 13
- 230000000707 stereoselective effect Effects 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 230000000694 effects Effects 0.000 claims abstract description 11
- 210000000496 pancreas Anatomy 0.000 claims abstract description 10
- 241000283973 Oryctolagus cuniculus Species 0.000 claims abstract description 4
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 32
- 238000006243 chemical reaction Methods 0.000 claims description 32
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 22
- 230000003287 optical effect Effects 0.000 claims description 16
- 238000006460 hydrolysis reaction Methods 0.000 claims description 13
- 150000007524 organic acids Chemical class 0.000 claims description 12
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims description 11
- 229910052921 ammonium sulfate Inorganic materials 0.000 claims description 11
- 235000011130 ammonium sulphate Nutrition 0.000 claims description 11
- 239000003960 organic solvent Substances 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 238000004440 column chromatography Methods 0.000 claims description 6
- 238000000605 extraction Methods 0.000 claims description 6
- 230000003301 hydrolyzing effect Effects 0.000 claims description 6
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 5
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000003456 ion exchange resin Substances 0.000 claims description 4
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 238000004508 fractional distillation Methods 0.000 claims description 3
- BGKABGGFJSTLIL-UHFFFAOYSA-N 3-(hydroxymethyl)-1,3-oxazolidin-2-one Chemical compound OCN1CCOC1=O BGKABGGFJSTLIL-UHFFFAOYSA-N 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 4
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- 108090000604 Hydrolases Proteins 0.000 claims 1
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 claims 1
- 239000012634 fragment Substances 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 241001465754 Metazoa Species 0.000 abstract description 4
- 230000004048 modification Effects 0.000 abstract 2
- 238000012986 modification Methods 0.000 abstract 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract 1
- 102000012740 beta Adrenergic Receptors Human genes 0.000 abstract 1
- 108010079452 beta Adrenergic Receptors Proteins 0.000 abstract 1
- 238000000354 decomposition reaction Methods 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- 229940088598 enzyme Drugs 0.000 description 40
- 239000000243 solution Substances 0.000 description 28
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 239000006228 supernatant Substances 0.000 description 18
- 239000002244 precipitate Substances 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000008363 phosphate buffer Substances 0.000 description 13
- 239000000758 substrate Substances 0.000 description 13
- MVRRMVWKCYWXSY-UHFFFAOYSA-N (2-oxo-3-propan-2-yl-1,3-oxazolidin-5-yl)methyl acetate Chemical compound CC(C)N1CC(COC(C)=O)OC1=O MVRRMVWKCYWXSY-UHFFFAOYSA-N 0.000 description 11
- 239000000203 mixture Substances 0.000 description 9
- 238000005119 centrifugation Methods 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- RXRVCSDDGFQDOJ-UHFFFAOYSA-N 5-(hydroxymethyl)-3-propan-2-yl-1,3-oxazolidin-2-one Chemical compound CC(C)N1CC(CO)OC1=O RXRVCSDDGFQDOJ-UHFFFAOYSA-N 0.000 description 7
- 210000001557 animal structure Anatomy 0.000 description 7
- 239000012141 concentrate Substances 0.000 description 7
- -1 p-methylbenzyl group Chemical group 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 6
- 239000002876 beta blocker Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 239000007788 liquid Substances 0.000 description 4
- GUBGYTABKSRVRQ-WFVLMXAXSA-N DEAE-cellulose Chemical compound OC1C(O)C(O)C(CO)O[C@H]1O[C@@H]1C(CO)OC(O)C(O)C1O GUBGYTABKSRVRQ-WFVLMXAXSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 235000010355 mannitol Nutrition 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- UZUMQQZPGOFJBQ-UHFFFAOYSA-N 1-aminopropane-1,2-diol Chemical class CC(O)C(N)O UZUMQQZPGOFJBQ-UHFFFAOYSA-N 0.000 description 2
- 241000283690 Bos taurus Species 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 108090001060 Lipase Proteins 0.000 description 2
- 239000004367 Lipase Substances 0.000 description 2
- 102000004882 Lipase Human genes 0.000 description 2
- 108010019160 Pancreatin Proteins 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 235000019421 lipase Nutrition 0.000 description 2
- 229940055695 pancreatin Drugs 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 108091016642 steapsin Proteins 0.000 description 2
- XUPZAARQDNSRJB-SJDTYFKWSA-N trans-dothiepin hydrochloride Chemical compound [Cl-].C1SC2=CC=CC=C2C(=C/CC[NH+](C)C)/C2=CC=CC=C21 XUPZAARQDNSRJB-SJDTYFKWSA-N 0.000 description 2
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
- 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- QWOJMRHUQHTCJG-UHFFFAOYSA-N CC([CH2-])=O Chemical compound CC([CH2-])=O QWOJMRHUQHTCJG-UHFFFAOYSA-N 0.000 description 1
- MNQZXJOMYWMBOU-VKHMYHEASA-N D-glyceraldehyde Chemical compound OC[C@@H](O)C=O MNQZXJOMYWMBOU-VKHMYHEASA-N 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000007073 chemical hydrolysis Effects 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- JEHCHYAKAXDFKV-UHFFFAOYSA-J lead tetraacetate Chemical compound CC(=O)O[Pb](OC(C)=O)(OC(C)=O)OC(C)=O JEHCHYAKAXDFKV-UHFFFAOYSA-J 0.000 description 1
- 229940040511 liver extract Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 229940062190 pancreas extract Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10193989A JPH01309696A (ja) | 1989-04-21 | 1989-04-21 | 光学活性オキサゾリジノン誘導体の製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10193989A JPH01309696A (ja) | 1989-04-21 | 1989-04-21 | 光学活性オキサゾリジノン誘導体の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01309696A true JPH01309696A (ja) | 1989-12-14 |
| JPH0534957B2 JPH0534957B2 (enrdf_load_stackoverflow) | 1993-05-25 |
Family
ID=14313875
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10193989A Granted JPH01309696A (ja) | 1989-04-21 | 1989-04-21 | 光学活性オキサゾリジノン誘導体の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01309696A (enrdf_load_stackoverflow) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5978696A (ja) * | 1982-10-28 | 1984-05-07 | Kanegafuchi Chem Ind Co Ltd | 光学活性オキサゾリジノン誘導体の製造方法 |
| JPS6078596A (ja) * | 1983-10-06 | 1985-05-04 | Kanegafuchi Chem Ind Co Ltd | 固定化酵素による光学活性オキサゾリジン誘導体の製造法 |
-
1989
- 1989-04-21 JP JP10193989A patent/JPH01309696A/ja active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5978696A (ja) * | 1982-10-28 | 1984-05-07 | Kanegafuchi Chem Ind Co Ltd | 光学活性オキサゾリジノン誘導体の製造方法 |
| JPS6078596A (ja) * | 1983-10-06 | 1985-05-04 | Kanegafuchi Chem Ind Co Ltd | 固定化酵素による光学活性オキサゾリジン誘導体の製造法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0534957B2 (enrdf_load_stackoverflow) | 1993-05-25 |
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