HRID34503

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID70297

Benzenecarboperoxoic acid, 3-chloro-

C7H5ClO3

HCID516892

Sodium Bicarbonate

CHNaO3

HCID23665763

Sodium Bisulfite

HNaO3S

结构：O=C(NC1C(=O)N2C(C(=O)OC(c3ccccc3)c3ccccc3)=C(CCl)CS[C@H]12)C(=NOC(F)F)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1

HCID131715668

未命名化合物

PRODUCTS

生成物

结构：O=C(NC1C(=O)N2C(C(=O)OC(c3ccccc3)c3ccccc3)=C(CCl)CS(=O)[C@H]12)C(=NOC(F)F)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1

HCID131715684

未命名化合物

收率 84%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID962

Water

H2O

溶剂HCID8857

Ethyl acetate

C4H8O2

PROCEDURE

实验过程

A mixture of benzhydryl 7-[2-(2-tritylaminothiazol-4-yl)-2-difluoromethoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylate (syn isomer) (35 g), m-chloroperbenzoic acid (8.64 g) and ethyl acetate (300 ml) was stirred for 30 minutes at 0° to 5° C. and then, water (300 ml), sodium bisulfite and sodium bicarbonate were added thereto. The organic layer was separated, washed with an aqueous solution of sodium chloride, dried over magnesium sulfate and evaporated. The residue was triturated with diisopropyl ether to give benzhydryl 7-[2-(2-tritylaminothiazol-4-yl)-2-difluoromethoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylate-1-oxide (syn isomer) (29.93 g).

WORKUP

后处理

customThe organic layer was separated
washwashed with an aqueous solution of sodium chloride
dry with materialdried over magnesium sulfate
customevaporated
customThe residue was triturated with diisopropyl ether

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-93268cfdc70447dbbff9ca9aaf842625
来源数据集: uspto-grants-1988_08
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04761410
来源说明: uspto-grants-1988_08

反应 SMILES

[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:57][O:58][CH:59]([F:61])[F:60])[C:27]([NH:29][CH:30]2[C:55](=[O:56])[N:32]3[C:33]([C:39]([O:41][CH:42]([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)=[O:40])=[C:34]([CH2:37][Cl:38])[CH2:35][S:36][C@H:31]23)=[O:28])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:70])C=1.S(=O)(O)[O-].[Na+].C(=O)(O)[O-].[Na+]>O.C(OCC)(=O)C>[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:57][O:58][CH:59]([F:61])[F:60])[C:27]([NH:29][CH:30]2[C:55](=[O:56])[N:32]3[C:33]([C:39]([O:41][CH:42]([C:49]4[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=4)[C:43]4[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=4)=[O:40])=[C:34]([CH2:37][Cl:38])[CH2:35][S:36](=[O:70])[C@H:31]23)=[O:28])[N:25]=1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1