HRID372868

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID6367

Acetyl chloride

C2H3ClO

结构：CC(=O)OC(C)C1=C(C(=O)OC(c2ccccc2)c2ccccc2)N2C(=O)C(NC(=O)Cc3cccs3)[C@H]2S(=O)C1

HCID70617865

未命名化合物

PRODUCTS

生成物

结构：CC(=O)OC(C)C1=C(C(=O)OC(c2ccccc2)c2ccccc2)N2C(=O)C(NC(=O)Cc3cccs3)[C@H]2SC1

HCID70617769

未命名化合物

收率 105.8%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

PROCEDURE

实验过程

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.

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-c6c0fd9703e04c669c3de6da24d994e0
来源数据集: uspto-grants-1978_05
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04092474
来源说明: uspto-grants-1978_05

反应 SMILES

[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]