JPS55111463A - Beta-lactam compound and its preparation - Google Patents
Beta-lactam compound and its preparationInfo
- Publication number
- JPS55111463A JPS55111463A JP1951279A JP1951279A JPS55111463A JP S55111463 A JPS55111463 A JP S55111463A JP 1951279 A JP1951279 A JP 1951279A JP 1951279 A JP1951279 A JP 1951279A JP S55111463 A JPS55111463 A JP S55111463A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- beta
- preparation
- acidolysis
- 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.)
- Pending
Links
- -1 Beta-lactam compound Chemical class 0.000 title abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 230000007062 hydrolysis Effects 0.000 abstract 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract 2
- 238000006894 reductive elimination reaction Methods 0.000 abstract 2
- WKDDRNSBRWANNC-UHFFFAOYSA-N Thienamycin Natural products C1C(SCCN)=C(C(O)=O)N2C(=O)C(C(O)C)C21 WKDDRNSBRWANNC-UHFFFAOYSA-N 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 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
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
NEW MATERIAL:A β-lactam compound of formula I (R1 is H or OH-protecting group, e.g. aliphatic or aromatic acyl, lower alkoxycarbonyl, halogeno-lower alkoxy- carbonyl, aralkyl group, etc.; R2 is H or COOH-protecting group, e.g. lower alkyl, halogeno-lower alkyl, aralkyl group, etc.).
EXAMPLE: 1-Carboxymethyl-3-(1'-hydroxyethyl)-4-carboxyazetidin-2-one.
USE: An intermediate for the synthesis of a thienamycin compound which is an antibacterial.
PROCESS: A compound of formula II (R3 is COOH-protecting groups; X is halogen) is treated with a base to give a compound of formula III, which is subjected to partial hydrolysis, reductive cleavage, or acidolysis to form a compound of formula IV, which is decarboxylated to afford a compound of formula V. The resulting compound is subjected to partial hydrolysis, reductive cleavage, or acidolysis to give the compound of formula I.
COPYRIGHT: (C)1980,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1951279A JPS55111463A (en) | 1979-02-21 | 1979-02-21 | Beta-lactam compound and its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1951279A JPS55111463A (en) | 1979-02-21 | 1979-02-21 | Beta-lactam compound and its preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS55111463A true JPS55111463A (en) | 1980-08-28 |
Family
ID=12001410
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1951279A Pending JPS55111463A (en) | 1979-02-21 | 1979-02-21 | Beta-lactam compound and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS55111463A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2518997A1 (en) * | 1981-12-30 | 1983-07-01 | Richter Gedeon Vegyeszet | NOVEL HETEROCYCLIC CARBOXYLIC ACIDS AND PROCESS FOR PREPARING THE SAME |
| FR2519339A1 (en) * | 1982-01-05 | 1983-07-08 | Richter Gedeon Vegyeszet | HETEROCYCLIC COMPOUNDS CONTAINING C-ACETYL GROUP AND PROCESS FOR PREPARING THE SAME |
| JPS59181254A (en) * | 1983-03-28 | 1984-10-15 | チバ−ガイギ−・アクチエンゲゼルシヤフト | Manufacture of optically active azetidinone |
| JPS6048964A (en) * | 1983-08-26 | 1985-03-16 | Sankyo Co Ltd | 2-azetidinone derivative and its preparation |
| JPS6051171A (en) * | 1983-08-30 | 1985-03-22 | Sankyo Co Ltd | Production of beta-lactam compound |
| JPS6054358A (en) * | 1983-08-04 | 1985-03-28 | フア−ミタリア・カルロ・エルバ・ソシエタ・ペル・アツイオ−ニ | Azetidinones |
| US4556514A (en) * | 1982-10-13 | 1985-12-03 | Sumitomo Chemical Company, Limited | 4-Carboxy azetidinone compounds and production thereof from diketene and a Schiff base |
| JPH0616622A (en) * | 1984-10-01 | 1994-01-25 | Ciba Geigy Ag | Azetidinone compound and its production |
-
1979
- 1979-02-21 JP JP1951279A patent/JPS55111463A/en active Pending
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2518997A1 (en) * | 1981-12-30 | 1983-07-01 | Richter Gedeon Vegyeszet | NOVEL HETEROCYCLIC CARBOXYLIC ACIDS AND PROCESS FOR PREPARING THE SAME |
| JPS58118565A (en) * | 1981-12-30 | 1983-07-14 | リヒテル・ゲデオン・ベギエスゼテイ・ギアル・ア−ル・テイ− | Novel heterocyclic carboxylic acid and manufacture |
| FR2519339A1 (en) * | 1982-01-05 | 1983-07-08 | Richter Gedeon Vegyeszet | HETEROCYCLIC COMPOUNDS CONTAINING C-ACETYL GROUP AND PROCESS FOR PREPARING THE SAME |
| US4556514A (en) * | 1982-10-13 | 1985-12-03 | Sumitomo Chemical Company, Limited | 4-Carboxy azetidinone compounds and production thereof from diketene and a Schiff base |
| JPS59181254A (en) * | 1983-03-28 | 1984-10-15 | チバ−ガイギ−・アクチエンゲゼルシヤフト | Manufacture of optically active azetidinone |
| JPS6054358A (en) * | 1983-08-04 | 1985-03-28 | フア−ミタリア・カルロ・エルバ・ソシエタ・ペル・アツイオ−ニ | Azetidinones |
| JPS6048964A (en) * | 1983-08-26 | 1985-03-16 | Sankyo Co Ltd | 2-azetidinone derivative and its preparation |
| JPS6051171A (en) * | 1983-08-30 | 1985-03-22 | Sankyo Co Ltd | Production of beta-lactam compound |
| JPH0616622A (en) * | 1984-10-01 | 1994-01-25 | Ciba Geigy Ag | Azetidinone compound and its production |
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