Acetyl chloride → Diphenylmethyl 7-(2-thienylacetamido)-3-(1-acetoxyethyl)-3-cephem-4-carboxylate

HRID 372868Notes

Reaction equation

HRID 372868 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:40](=[O:41])[N:12]2[C:13]([C:24]([O:26][CH:27]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:25])=[C:14]([CH:18]([O:20][C:21](=[O:23])[CH3:22])[CH3:19])[CH2:15][S:16](=O)[C@H:11]12)=[O:8].C(Cl)(=O)C>CN(C)C=O>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:40](=[O:41])[N:12]2[C:13]([C:24]([O:26][CH:27]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)=[O:25])=[C:14]([CH:18]([O:20][C:21](=[O:23])[CH3:22])[CH3:19])[CH2:15][S:16][C@H:11]12)=[O:8]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 70617865Diphenylmethyl 7-(2-thienylacetamido)-3-(1-acetoxyethyl)-3-cephem-4-carboxylate 1-oxide

Product 1

HCID 70617769Diphenylmethyl 7-(2-thienylacetamido)-3-(1-acetoxyethyl)-3-cephem-4-carboxylateYield 105.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Similarly, polar isomer B of diphenylmethyl 7-(2-thienylacetamido)-3-(1-acetoxyethyl)-3-cephem-4-carboxylate 1-oxide (69 mg) is reduced with stannous chloride dihydrate (66 mg) and acetyl chloride (0.28 ml) in N,N-dimethylformamide (2.1 ml) for 15 minutes to give stereoisomer B of diphenylmethyl 7-(2-thienylacetamido)-3-(1-acetoxyethyl)-3-cephem-4-carboxylate (71 mg). m.p. 72°-80° C. Yield: 83.4%. IR: νmaxCHCl 3 3396, 1787, 1731, 1687, 1508 cm-1. NMR: δCDCl 3 1.27d(6.5Hz) 3H, 1.88s3H, 3.40br-s2H, 3.83s2H, 4.95d(5Hz)1H, 5.72q(9;5Hz) 1H, 6.11q(6.5Hz)1H, 6.48d(9Hz)1H, 6.9-7.5m14H.

Sources & evidence

ORD record
ord-c6c0fd9703e04c669c3de6da24d994e0
Source dataset
uspto-grants-1978_05
Patent number
US04092474

Reaction notes

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