JPS54100392A - Production of cephalosporin derivative - Google Patents
Production of cephalosporin derivativeInfo
- Publication number
- JPS54100392A JPS54100392A JP631378A JP631378A JPS54100392A JP S54100392 A JPS54100392 A JP S54100392A JP 631378 A JP631378 A JP 631378A JP 631378 A JP631378 A JP 631378A JP S54100392 A JPS54100392 A JP S54100392A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- chloride
- group
- production
- 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
- 229930186147 Cephalosporin Natural products 0.000 title abstract 2
- 229940124587 cephalosporin Drugs 0.000 title abstract 2
- 150000001780 cephalosporins Chemical class 0.000 title 1
- -1 hydroxyacetylamino group Chemical group 0.000 abstract 3
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 abstract 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 abstract 1
- 125000003460 beta-lactamyl group Chemical group 0.000 abstract 1
- 230000003115 biocidal effect Effects 0.000 abstract 1
- 125000001271 cephalosporin group Chemical group 0.000 abstract 1
- FRYHCSODNHYDPU-UHFFFAOYSA-N ethanesulfonyl chloride Chemical compound CCS(Cl)(=O)=O FRYHCSODNHYDPU-UHFFFAOYSA-N 0.000 abstract 1
- 125000000524 functional group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 230000026030 halogenation Effects 0.000 abstract 1
- 238000005658 halogenation reaction Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 abstract 1
- 125000006239 protecting group Chemical group 0.000 abstract 1
- 238000006277 sulfonation 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
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-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
- Cephalosporin Compounds (AREA)
Abstract
PURPOSE: The hydroxyl group of hydroxyacetylamino group in the 7-position of cephalosporin is selectively halogenated or sulfonated without giving damage to β- lactam ring and other functional groups to prepare title compound useful for antibiotic or its synthetic intermediate.
CONSTITUTION: A compound of formula I (R1 is H, methoxy; R2 is H, lower acyloxy, heterocyclic thio, carbamoyloxy; R3 is H or protecting group) is reacted with a halogenation agent as thionyl chloride, thionyl bromide or phosphorus trichloride, or sulfonation agent as methanesulfonyl chloride or ethanesulfonyl chloride in an inert solvent in the presence of a base to produce a compound of formula II(X is halogen, alkylsulfonyloxy, arylsulfonyloxy).
COPYRIGHT: (C)1979,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP631378A JPS54100392A (en) | 1978-01-24 | 1978-01-24 | Production of cephalosporin derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP631378A JPS54100392A (en) | 1978-01-24 | 1978-01-24 | Production of cephalosporin derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS54100392A true JPS54100392A (en) | 1979-08-08 |
Family
ID=11634872
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP631378A Pending JPS54100392A (en) | 1978-01-24 | 1978-01-24 | Production of cephalosporin derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS54100392A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55153791A (en) * | 1979-05-18 | 1980-11-29 | Sumitomo Chem Co Ltd | Novel beta-lactam compound |
| JPS5665895A (en) * | 1979-10-31 | 1981-06-03 | Sumitomo Chem Co Ltd | Novel 7alpha-methoxycephalosporin compound |
| JPS6242989A (en) * | 1986-08-04 | 1987-02-24 | Sumitomo Pharmaceut Co Ltd | Production of 7alpha-methoxycephalosporin compound |
| EP1132391A4 (en) * | 1999-09-20 | 2002-06-12 | Otsuka Kagaku Kk | Process for the preparation of 3-sulfonyloxy-3-cephem compounds |
-
1978
- 1978-01-24 JP JP631378A patent/JPS54100392A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55153791A (en) * | 1979-05-18 | 1980-11-29 | Sumitomo Chem Co Ltd | Novel beta-lactam compound |
| JPS5665895A (en) * | 1979-10-31 | 1981-06-03 | Sumitomo Chem Co Ltd | Novel 7alpha-methoxycephalosporin compound |
| JPS6242989A (en) * | 1986-08-04 | 1987-02-24 | Sumitomo Pharmaceut Co Ltd | Production of 7alpha-methoxycephalosporin compound |
| EP1132391A4 (en) * | 1999-09-20 | 2002-06-12 | Otsuka Kagaku Kk | Process for the preparation of 3-sulfonyloxy-3-cephem compounds |
| KR100439491B1 (en) * | 1999-09-20 | 2004-07-14 | 오쯔까 가가꾸 가부시키가이샤 | Process for the preparation of 3-sulfonyloxy-3-cephem compounds |
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