HRID980990

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID5238

Sodium Iodide

INa

HCID11776

Triphenylphosphine

C18H15P

结构：CCON=C(C(=O)NC1C(=O)N2C(C(=O)OC(c3ccccc3)c3ccccc3)=C(CCl)CS[C@H]12)c1nsc(N)n1

HCID131714229

未命名化合物

PRODUCTS

生成物

结构：CCON=C(C(=O)NC1C(=O)N2C(C(=O)OC(c3ccccc3)c3ccccc3)=C(C[P+](c3ccccc3)(c3ccccc3)c3ccccc3)CS[C@H]12)c1nsc(N)n1.[Cl-]

HCID131714367

未命名化合物

收率 59.4%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID8857

Ethyl acetate

C4H8O2

PROCEDURE

实验过程

A mixture of benzhydryl 7-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylate (syn isomer) (36.7 g) in ethyl acetate (600 ml), triphenyl phosphine (18.8 g) and sodium iodide (1 g) were boiled under reflux for 100 minutes. The precipitates were collected by filtration and washed with ethyl acetate to give [4-benzhydryloxycarbonyl-7-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetamido]-3-cephem-3-ylmethyl]triphenylphosphonium chloride (syn isomer)(31.1 g).

WORKUP

后处理

temperatureunder reflux for 100 minutes
filtrationThe precipitates were collected by filtration
washwashed with ethyl acetate

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-5fd003959a164c58903ed81e2d2dbb64
来源数据集: uspto-grants-1987_01
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04639448
来源说明: uspto-grants-1987_01

反应 SMILES

[NH2:1][C:2]1[S:6][N:5]=[C:4]([C:7](=[N:38][O:39][CH2:40][CH3:41])[C:8]([NH:10][CH:11]2[C:36](=[O:37])[N:13]3[C:14]([C:20]([O:22][CH:23]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[O:21])=[C:15]([CH2:18][Cl:19])[CH2:16][S:17][C@H:12]23)=[O:9])[N:3]=1.[C:42]1([P:48]([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1.[I-].[Na+]>C(OCC)(=O)C>[Cl-:19].[CH:23]([O:22][C:20]([C:14]1[N:13]2[C:36](=[O:37])[CH:11]([NH:10][C:8](=[O:9])[C:7]([C:4]3[N:3]=[C:2]([NH2:1])[S:6][N:5]=3)=[N:38][O:39][CH2:40][CH3:41])[C@H:12]2[S:17][CH2:16][C:15]=1[CH2:18][P+:48]([C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)[C:55]1[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=1)=[O:21])([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1