Hydrochloric Acid → 7-(2-Methoxyimino-3-oxo-bromobutyramido)-3-cephem-4-carboxylic acid

HRID 1702078Notes

Reaction equation

C(OC(=O)C)(=O)C.C([O-])(=O)C.[Na+].[CH3:13][O:14][N:15]=[C:16]([C:36](=[O:39])[CH2:37][Br:38])[C:17]([NH:19][CH:20]1[C:34](=[O:35])[N:22]2[CH:23]([C:31]([OH:33])=[O:32])[CH:24](OC(=O)C)[CH2:25][S:26][C@H:21]12)=[O:18].Cl>CN(C)C=O.O1CCCC1>[CH3:13][O:14][N:15]=[C:16]([C:36](=[O:39])[CH2:37][Br:38])[C:17]([NH:19][CH:20]1[C:34](=[O:35])[N:22]2[C:23]([C:31]([OH:33])=[O:32])=[CH:24][CH2:25][S:26][C@H:21]12)=[O:18]

Participants

Conditions

Temperature: 28 °C

Procedure

Acetic anhydride (0.2 ml.), sodium acetate (0.12 g.) and N,N-dimethylformamide (2 drops) were added to a solution of 7-(2-methoxyimino-3-oxo-4-bromobutyramido)3-acetoxy-cepham-4-carboxylic acid (syn isomer, 200 mg.) in dry tetrahydrofuran (2 ml.), and stirred at 28° C. for an hour. 6 N Hydrochloric acid (0.2 ml.) was added to the resultant solution and the solvent was evaporated in vacuo. Water was added to the residue. The precipitates were collected by filtration, washed with water and dried to give a mixture (0.09 g.) of 7-(2-methoxyimino-3-oxo-4-bromobutyramido)-3-cephem-4-carboxylic acid (syn isomer) and 7-(2-methoxyimino-3-oxo-4-chlorobutyramido)-3-cephem-3-carboxylic acid (syn isomer). [7-(2-methoxyimino-3-oxo-4-bromobutyramido)-3-cephem-4-carboxylic acid (syn isomer)]

Workup

customthe solvent was evaporated in vacuo
additionWater was added to the residue
filtrationThe precipitates were collected by filtration
washwashed with water
customdried

Sources & evidence

ORD record: ord-d88d689aff17414381d8e9958a0f4a74
Source dataset: uspto-grants-1983_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04379922

Reaction notes

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