Diazomethane → 7beta-[2-(2-Carbobenzoxyamino-5-fluoro-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid diphenylmethyl ester

HRID 126902Notes

Reaction equation

HRID 126902 reaction equation
[C:1]1([CH:7]([O:14][C:15]([C:17]2[N:22]3[C:23](=[O:48])[C@@H:24]([NH:25][C:26](=[O:47])[C:27]([C:30]4[N:31]=[C:32]([NH:36][C:37]([O:39][CH2:40][C:41]5[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=5)=[O:38])[S:33][C:34]=4[F:35])=[N:28][OH:29])[C@H:21]3[S:20][CH2:19][CH:18]=2)=[O:16])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+](=[CH2:51])=[N-]>ClCCl.CCOCC>[C:1]1([CH:7]([O:14][C:15]([C:17]2[N:22]3[C:23](=[O:48])[C@@H:24]([NH:25][C:26](=[O:47])[C:27]([C:30]4[N:31]=[C:32]([NH:36][C:37]([O:39][CH2:40][C:41]5[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=5)=[O:38])[S:33][C:34]=4[F:35])=[N:28][O:29][CH3:51])[C@H:21]3[S:20][CH2:19][CH:18]=2)=[O:16])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 1317121067beta-[2-(2-Carbobenzoxyamino-5-fluoro-4-thiazolyl)-2-hydroxyiminoacetamido]-3-cephem-4-carboxylic acid diphenylmethyl ester

Product 1

HCID 1317121007beta-[2-(2-Carbobenzoxyamino-5-fluoro-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid diphenylmethyl ester

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 7β-[2-(2-carbobenzoxyamino-5-fluoro-4-thiazolyl)-2-hydroxyiminoacetamido]-3-cephem-4-carboxylic acid diphenylmethyl ester (180 mg) in dichloromethane (3 ml) is added a solution of diazomethane in ether until yellow color of the solution does no more fade out. After 30 minutes, the reaction mixture is concentrated to give 7β-[2-(2-carbobenzoxyamino-5-fluoro-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid diphenylmethyl ester (153 mg). Similarly prepared are compounds of Table 1.

Workup

  1. concentrationthe reaction mixture is concentrated

Sources & evidence

ORD record
ord-b029a3f3f3cb483cb559a307be877291
Source dataset
uspto-grants-1981_03
Patent number
US04254119

Reaction notes

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