7-amino-3-(1-carboxymethyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid → 7-[2-ethoxyimino-2-(2-formamido-1,3-thiazol-4-yl)acetamido]-3-(1-carboxymethyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid

HRID 648413Notes

Reaction equation

HRID 648413 reaction equation
[CH2:1]([O:3][N:4]=[C:5]([C:9]1[N:10]=[C:11]([NH:14][CH:15]=[O:16])[S:12][CH:13]=1)[C:6]([OH:8])=O)[CH3:2].[NH2:17][CH:18]1[C:39](=[O:40])[N:20]2[C:21]([C:36]([OH:38])=[O:37])=[C:22]([CH2:25][S:26][C:27]3[N:31]([CH2:32][C:33]([OH:35])=[O:34])[N:30]=[N:29][N:28]=3)[CH2:23][S:24][C@H:19]12>>[CH2:1]([O:3][N:4]=[C:5]([C:9]1[N:10]=[C:11]([NH:14][CH:15]=[O:16])[S:12][CH:13]=1)[C:6]([NH:17][CH:18]1[C:39](=[O:40])[N:20]2[C:21]([C:36]([OH:38])=[O:37])=[C:22]([CH2:25][S:26][C:27]3[N:31]([CH2:32][C:33]([OH:35])=[O:34])[N:30]=[N:29][N:28]=3)[CH2:23][S:24][C@H:19]12)=[O:8])[CH3:2]

Participants

3

Reactant 2

HCID 127691497-amino-3-(1-carboxymethyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acidHCID 544580772-(2-Formamidothiazol-4-yl)-2-ethoxyiminoacetic acid

Product 1

HCID 1317124057-[2-ethoxyimino-2-(2-formamido-1,3-thiazol-4-yl)acetamido]-3-(1-carboxymethyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acidYield 54.4%

Procedure

2-Ethoxyimino-2-(2-formamido-1,3-thiazol-4-yl)acetic acid (syn isomer) (3.0 g.) and 7-amino-3-(1-carboxymethyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (4.12 g.) were reacted according to similar to those of Examples 1(b), 2(b), 3(b) and 6(b) to give 7-[2-ethoxyimino-2-(2-formamido-1,3-thiazol-4-yl)acetamido]-3-(1-carboxymethyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (3.6 g.).

Sources & evidence

ORD record
ord-9862cac4902941119d8482729c2623cd
Source dataset
uspto-grants-1983_10
Patent number
US04411898

Reaction notes

Loading…