Diisopropyl Ether → 7-[2-(2-Amino-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid

HRID 1154825Notes

Reaction equation

[CH3:1][O:2][N:3]=[C:4]([C:20](=O)[CH2:21]Br)[C:5]([NH:7][CH:8]1[C:18](=[O:19])[N:10]2[C:11]([C:15]([OH:17])=[O:16])=[CH:12][CH2:13][S:14][C@H:9]12)=[O:6].[NH2:24][C:25]([NH2:27])=[S:26].C([O-])(=O)C.[Na+].C(OC(C)C)(C)C>CO>[NH2:27][C:25]1[S:26][CH:21]=[C:20]([C:4](=[N:3][O:2][CH3:1])[C:5]([NH:7][CH:8]2[C:18](=[O:19])[N:10]3[C:11]([C:15]([OH:17])=[O:16])=[CH:12][CH2:13][S:14][C@H:9]23)=[O:6])[N:24]=1

Participants

Conditions

Temperature: 30 °C

Procedure

7-(2-Methoxyimino-3-oxo-4-bromobutyramido)-3-cephem-4-carboxylic acid (syn isomer, 10 g.) was added to a solution of thiourea (2.81 g.) and sodium acetate (2.22 g.) in methanol (50 ml) and stirred at 30° C. for 5 hours. To the resultant solution was added diisopropyl ether (200 ml.) and stirred at 30 minutes. The precipitates were collected by filtration, washed with diisopropyl ether and dried to give 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid (syn isomer, 11.2 g.).

Workup

stirringstirred at 30 minutes
filtrationThe precipitates were collected by filtration
washwashed with diisopropyl ether
customdried

Sources & evidence

ORD record: ord-0479a36bb51b4f699bed390f897e9061
Source dataset: uspto-grants-1981_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04298529

Reaction notes

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