JPH0242476B2 - - Google Patents
Info
- Publication number
- JPH0242476B2 JPH0242476B2 JP55146344A JP14634480A JPH0242476B2 JP H0242476 B2 JPH0242476 B2 JP H0242476B2 JP 55146344 A JP55146344 A JP 55146344A JP 14634480 A JP14634480 A JP 14634480A JP H0242476 B2 JPH0242476 B2 JP H0242476B2
- Authority
- JP
- Japan
- Prior art keywords
- ester
- group
- optically active
- amino
- protecting group
- 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.)
- Expired - Lifetime
Links
- 150000002148 esters Chemical class 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 210000004185 liver Anatomy 0.000 claims description 6
- 125000006239 protecting group Chemical group 0.000 claims description 6
- 238000010531 catalytic reduction reaction Methods 0.000 claims description 5
- 125000004185 ester group Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 230000008030 elimination Effects 0.000 claims description 2
- 238000003379 elimination reaction Methods 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 12
- -1 β-lactam compounds Chemical class 0.000 description 8
- 108090000790 Enzymes Proteins 0.000 description 7
- 102000004190 Enzymes Human genes 0.000 description 7
- 125000003277 amino group Chemical group 0.000 description 7
- 229940088598 enzyme Drugs 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 108090000371 Esterases Proteins 0.000 description 4
- 108090000604 Hydrolases Proteins 0.000 description 4
- 102000004157 Hydrolases Human genes 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 230000002255 enzymatic effect Effects 0.000 description 4
- CTLHFZBIZFOLIK-BYPYZUCNSA-N (3s)-3-amino-5-methoxy-5-oxopentanoic acid Chemical compound COC(=O)C[C@@H](N)CC(O)=O CTLHFZBIZFOLIK-BYPYZUCNSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- WKDDRNSBRWANNC-ATRFCDNQSA-N Thienamycin Chemical compound C1C(SCCN)=C(C(O)=O)N2C(=O)[C@H]([C@H](O)C)[C@H]21 WKDDRNSBRWANNC-ATRFCDNQSA-N 0.000 description 3
- WKDDRNSBRWANNC-UHFFFAOYSA-N Thienamycin Natural products C1C(SCCN)=C(C(O)=O)N2C(=O)C(C(O)C)C21 WKDDRNSBRWANNC-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- BBJIPMIXTXKYLZ-UHFFFAOYSA-N isoglutamic acid Chemical compound OC(=O)CC(N)CC(O)=O BBJIPMIXTXKYLZ-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- RBOKYBCBRQCEHG-NSHDSACASA-N (3s)-5-methoxy-5-oxo-3-(phenylmethoxycarbonylamino)pentanoic acid Chemical compound COC(=O)C[C@H](CC(O)=O)NC(=O)OCC1=CC=CC=C1 RBOKYBCBRQCEHG-NSHDSACASA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 2
- 108010027597 alpha-chymotrypsin Proteins 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- GCARTCPMCGRKDU-UHFFFAOYSA-N dimethyl 3-(phenylmethoxycarbonylamino)pentanedioate Chemical compound COC(=O)CC(CC(=O)OC)NC(=O)OCC1=CC=CC=C1 GCARTCPMCGRKDU-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000008363 phosphate buffer Substances 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 150000003952 β-lactams Chemical class 0.000 description 2
- 229930186147 Cephalosporin Natural products 0.000 description 1
- CKLJMWTZIZZHCS-UHFFFAOYSA-N D-OH-Asp Natural products OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-N 0.000 description 1
- 241000192125 Firmicutes Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CKLJMWTZIZZHCS-UWTATZPHSA-N L-Aspartic acid Natural products OC(=O)[C@H](N)CC(O)=O CKLJMWTZIZZHCS-UWTATZPHSA-N 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- SEWIYICDCVPBEW-BYPYZUCNSA-N L-glutamate methyl ester Chemical compound COC(=O)[C@@H](N)CCC(O)=O SEWIYICDCVPBEW-BYPYZUCNSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- 239000004365 Protease Substances 0.000 description 1
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 241000191940 Staphylococcus Species 0.000 description 1
- 125000005079 alkoxycarbonylmethyl group Chemical group 0.000 description 1
- 229940024606 amino acid Drugs 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 description 1
- 229960005261 aspartic acid Drugs 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical class O=C1CCN1 MNFORVFSTILPAW-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
- 150000001576 beta-amino acids Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- OGQXJNCMYDZGIJ-INWUZDNDSA-N carbapenam Chemical class C1CC(C(O)=O)N2C(=O)C(C)[C@H]21 OGQXJNCMYDZGIJ-INWUZDNDSA-N 0.000 description 1
- 229940041011 carbapenems Drugs 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- XDMNLFNTEOJHIZ-UHFFFAOYSA-N diethyl 3-(benzhydrylamino)pentanedioate Chemical compound C=1C=CC=CC=1C(NC(CC(=O)OCC)CC(=O)OCC)C1=CC=CC=C1 XDMNLFNTEOJHIZ-UHFFFAOYSA-N 0.000 description 1
- LUTOGWKCFUKNRU-UHFFFAOYSA-N diethyl 3-acetamidopentanedioate Chemical compound CCOC(=O)CC(NC(C)=O)CC(=O)OCC LUTOGWKCFUKNRU-UHFFFAOYSA-N 0.000 description 1
- GDPOAFNYCGJPME-UHFFFAOYSA-N dimethyl 2-(phenylmethoxycarbonylamino)pentanedioate Chemical compound COC(=O)CCC(C(=O)OC)NC(=O)OCC1=CC=CC=C1 GDPOAFNYCGJPME-UHFFFAOYSA-N 0.000 description 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 238000010647 peptide synthesis reaction Methods 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55146344A JPS5771394A (en) | 1980-10-21 | 1980-10-21 | Preparation of optically active monoalkyl beta-(s)-aminoglutarate |
| DE8181108343T DE3167862D1 (en) | 1980-10-21 | 1981-10-15 | New processes for the production of di-alkyl esters and optically active mono-alkyl esters of 3-aminoglutaric acid |
| EP81108343A EP0050799B1 (en) | 1980-10-21 | 1981-10-15 | New processes for the production of di-alkyl esters and optically active mono-alkyl esters of 3-aminoglutaric acid |
| AT81108343T ATE10835T1 (de) | 1980-10-21 | 1981-10-15 | Verfahren zur produktion von di-alkylestern und optisch aktiven mono-alkylestern von 3aminoglutars[ure. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55146344A JPS5771394A (en) | 1980-10-21 | 1980-10-21 | Preparation of optically active monoalkyl beta-(s)-aminoglutarate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5771394A JPS5771394A (en) | 1982-05-04 |
| JPH0242476B2 true JPH0242476B2 (zh) | 1990-09-21 |
Family
ID=15405574
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP55146344A Granted JPS5771394A (en) | 1980-10-21 | 1980-10-21 | Preparation of optically active monoalkyl beta-(s)-aminoglutarate |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5771394A (zh) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006075032A (ja) * | 2004-09-08 | 2006-03-23 | Ube Ind Ltd | 光学活性（ｒ又はｓ）−３−アミノグルタル酸モノエステル化合物の製造方法 |
| JP2010183917A (ja) * | 2010-06-01 | 2010-08-26 | Ube Ind Ltd | 光学活性（ｒ又はｓ）−３−アミノグルタル酸モノエステル化合物の製造方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56127380A (en) * | 1980-03-12 | 1981-10-06 | Toyama Chem Co Ltd | 2r,5r -3-oxo-7-oxo-1-azabicyclo 3,2,0 heptane-2-carboxylic acids and their preparations |
-
1980
- 1980-10-21 JP JP55146344A patent/JPS5771394A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56127380A (en) * | 1980-03-12 | 1981-10-06 | Toyama Chem Co Ltd | 2r,5r -3-oxo-7-oxo-1-azabicyclo 3,2,0 heptane-2-carboxylic acids and their preparations |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5771394A (en) | 1982-05-04 |
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