HRID1248773

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID962

Water

H2O

HCID70297

Benzenecarboperoxoic acid, 3-chloro-

C7H5ClO3

$结构：CO/N=C(\C(=O)NC1C(=O)N2C(C(=O)OC(c3ccccc3)c3ccccc3)=C(CI)CS[C@H]12)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1$

HCID13239634

未命名化合物

PRODUCTS

生成物

$结构：CO/N=C(\C(=O)NC1C(=O)N2C(C(=O)OC(c3ccccc3)c3ccccc3)=C(CI)CS(=O)[C@H]12)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1$

HCID13982441

未命名化合物

收率 99.3%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6344

Dichloromethane

CH2Cl2

CONDITIONS

反应条件

温度: 0 °C

PROCEDURE

实验过程

A mixture of benzhydryl 3-iodomethyl-7-[(Z)-2-methoxyimino-2-(2-tritylaminothiazol-4-yl)acetamido]-3-cephem-4-carboxylate (VIIa) (1.10 g, 1.19 mmoles) and m-chloroperbenzoic acid (m-CPBA) (322 mg, 1.30 mmoles) in CH2Cl2 (22 ml) was stirred at 0° C. for 15 minutes, poured into H2O (50 ml), and then extracted with CHCl3 (50 ml×3). The combined extracts were washed with saturated aqueous NaHCO3 (50 ml) and NaCl successively, dried and evaporated to afford the title compound (VIIa 1-oxide) (1.12 g, quantitative) as an amorphous powder.

WORKUP

后处理

extractionextracted with CHCl3 (50 ml×3)
washThe combined extracts were washed with saturated aqueous NaHCO3 (50 ml) and NaCl successively
customdried
customevaporated

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-7d984f2409814325a5750a6a1d1056c1
来源数据集: uspto-grants-1985_06
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04525473
来源说明: uspto-grants-1985_06

反应 SMILES

[I:1][CH2:2][C:3]1[CH2:4][S:5][C@@H:6]2[CH:26]([NH:27][C:28](=[O:58])/[C:29](=[N:55]\[O:56][CH3:57])/[C:30]3[N:31]=[C:32]([NH:35][C:36]([C:49]4[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=4)([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)[C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[S:33][CH:34]=3)[C:25](=[O:59])[N:7]2[C:8]=1[C:9]([O:11][CH:12]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10].ClC1C=CC=C(C(OO)=[O:68])C=1.O>C(Cl)Cl>[I:1][CH2:2][C:3]1[CH2:4][S:5](=[O:68])[C@@H:6]2[CH:26]([NH:27][C:28](=[O:58])/[C:29](=[N:55]\[O:56][CH3:57])/[C:30]3[N:31]=[C:32]([NH:35][C:36]([C:43]4[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=4)([C:49]4[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=4)[C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=4)[S:33][CH:34]=3)[C:25](=[O:59])[N:7]2[C:8]=1[C:9]([O:11][CH:12]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:10]