Ethyl Acetate → Diphenylmethyl 7beta-formamido-3-[(1,2,3-thiadiazol-5-yl)thio]-3-cephem-4-carboxylate

HRID 992687Notes

Reaction equation

[CH:1]([NH:3][C@@H:4]1[C:32](=[O:33])[N:6]2[C:7]([C:16]([O:18][CH:19]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:17])=[C:8](OS(C)(=O)=O)[CH2:9][S:10][C@H:5]12)=[O:2].[Na].[SH:35][C:36]1[S:40][N:39]=[N:38][CH:37]=1.C(OCC)(=O)C>CN(C=O)C>[CH:1]([NH:3][C@@H:4]1[C:32](=[O:33])[N:6]2[C:7]([C:16]([O:18][CH:19]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[O:17])=[C:8]([S:35][C:36]3[S:40][N:39]=[N:38][CH:37]=3)[CH2:9][S:10][C@H:5]12)=[O:2]

Participants

Conditions

Temperature: -20 °C

Procedure

To a solution of diphenylmethyl 7β-formamido-3-methanesulfonyloxy-3-cephem-4-carboxylate (1 g) in DMF (10 ml) was added sodium salt of 5-mercapto-1,2,3-thiadiazole (445 mg) at −30° C. After being stirred at −20° C. for 1 hour, the mixture was poured into a mixture of ice water and ethyl acetate. The organic layer was separated washed with water and brine, dried over magnesium sulfate, and evaporated to give diphenylmethyl 7β-formamido-3-[(1,2,3-thiadiazol-5-yl)thio]-3-cephem-4-carboxylate (961 mg).

Workup

customThe organic layer was separated
washwashed with water and brine
dry with materialdried over magnesium sulfate
customevaporated

Sources & evidence

ORD record: ord-dc21ee5a53d540c6a6e01aa80d64226b
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06468995B1

Reaction notes

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