Ethyl Acetate → 1-Propionyloxyethyl 7-[2-benzhydryloxycarbonylmethoxyimino-2-(4-thiazolyl)acetamido]-3-cephem-4-carboxylate

HRID 648846Notes

Reaction equation

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

Participants

Conditions

Temperature: 40 °C

Procedure

1-Chloroethyl propionate (0.6 g) was added to the mixture of 7-[2-benzhydryloxycarbonylmethoxyimino-2-(4-thiazolyl)acetamido]-3-cephem-4-carboxylic acid (syn isomer) (2.0 g) in dimethyl sulfoxide (13 ml) and potassium carbonate (0.3 g) and the mixture was stirred for 2 hours at 40° C. The reaction mixture was added to the mixture of ice-water and ethyl acetate and the mixture was adjusted to pH 7.5 with 20% aqueous solution of potassium carbonate. The separated organic layer was washed with water, dried over magnesium sulfate and evaporated to give 1-propionyloxyethyl 7-[2-benzhydryloxycarbonylmethoxyimino-2-(4-thiazolyl)acetamido]-3-cephem-4-carboxylate (syn isomer) (1.3 g).

Workup

washThe separated organic layer was washed with water
dry with materialdried over magnesium sulfate
customevaporated

Sources & evidence

ORD record: ord-6094b92f39454b86b11ef93565be82f4
Source dataset: uspto-grants-1988_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04736039

Reaction notes

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