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

HRID 372867Notes

Reaction equation

HRID 372867 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 79.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of non-polar stereoisomer A of diphenylmethyl 7-(2-thienylacetamido)-3-(1-acetoxyethyl)-3-cephem-4-carboxylate 1-oxide (85 mg) in N,N-dimethylformamide (2.5 ml) is added under ice cooling stannous chloride dihydrate (81 mg) with stirring. Ten minutes after the addition of acetyl chloride (0.34 mg), the mixture is stirred with ice for 20 minutes. The reaction mixture is poured into ice water, and is extracted with ethyl acetate. The extract solution is washed with aqueous sodium hydrogen carbonate and saline, dried over sodium sulfate, and evaporated. Recrystallization of the residue (81 mg) from petroleum ether gives the stereoisomer A of diphenylmethyl 7-(2-thienylacetamido)-3-(1-acetoxyethyl)-3-cephem-4-carboxylate (66 mg). m.p. 77°-85° C. Yield: 79.8%. IR: νmaxCHCl 3 3405, 1789, 1728, 1685, 1509 cm-1. NMR: δCDCl 3 1.34d(6.5Hz)3H, 1.98s3H, 3.37s2H, 3.82s2H, 4.96d(5Hz)1H, 5.79q (8.5;5Hz)1H, 5.99q(6.5Hz)1H, 6.32d(8.5Hz)1H, 6.8-7.5m14H.

Workup

  1. stirringthe mixture is stirred with ice for 20 minutes
  2. extractionis extracted with ethyl acetate
  3. washThe extract solution is washed with aqueous sodium hydrogen carbonate and saline
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customRecrystallization of the residue (81 mg) from petroleum ether

Sources & evidence

ORD record
ord-b2e1db508b774399bf7a1d6917775806
Source dataset
uspto-grants-1978_05
Patent number
US04092474

Reaction notes

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