Sodium Acetate → Benzhydryl 7-[2-benzyloxycarbonylmethoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-vinyl-3-cephem-4-carboxylate

HRID 1154261Notes

Reaction equation

[CH2:1]([O:8][C:9]([CH2:11][O:12][N:13]=[C:14]([C:45](=O)[CH2:46]Br)[C:15]([NH:17][CH:18]1[C:43](=[O:44])[N:20]2[C:21]([C:27]([O:29][CH:30]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[O:28])=[C:22]([CH:25]=[CH2:26])[CH2:23][S:24][C@H:19]12)=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:49][C:50]([NH2:52])=[S:51].C([O-])(=O)C.[Na+]>O1CCCC1.O>[CH2:1]([O:8][C:9]([CH2:11][O:12][N:13]=[C:14]([C:45]1[N:49]=[C:50]([NH2:52])[S:51][CH:46]=1)[C:15]([NH:17][CH:18]1[C:43](=[O:44])[N:20]2[C:21]([C:27]([O:29][CH:30]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)=[O:28])=[C:22]([CH:25]=[CH2:26])[CH2:23][S:24][C@H:19]12)=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 35 °C

Procedure

To a solution of benzhydryl 7-(2-benzyloxycarbonylmethoxyimino-4-bromo-3-oxobutyramido)-3-vinyl-3-cephem-4-carboxylate (2.5 g) in tetrahydrofuran (25 ml) was added a solution of thiourea (0.78 g) and sodium acetate (0.34 g) in water (10 ml), followed by stirring at 35° C. for 4 hours. The reaction mixture was extracted with ethyl acetate, and the extract was washed with a saturated aqueous sodium chloride and dried over magnesium sulfate. Removal of the solvent gave benzhydryl 7-[2-benzyloxycarbonylmethoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-vinyl-3-cephem-4-carboxylate (syn isomer) (2.0 g).

Workup

extractionThe reaction mixture was extracted with ethyl acetate
washthe extract was washed with a saturated aqueous sodium chloride
dry with materialdried over magnesium sulfate
customRemoval of the solvent

Sources & evidence

ORD record: ord-03ba2defad3a4d93b2ad6e2de220167d
Source dataset: uspto-grants-1984_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04487927

Reaction notes

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