HRID2309090

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID11776

Triphenylphosphine

C18H15P

结构：CO[C@H]1C(=O)N(C(Cl)C(=O)OCc2ccc([N+](=O)[O-])cc2)[C@@H]1SC(C)=O

HCID56613249

未命名化合物

PRODUCTS

生成物

结构：CO[C@H]1C(=O)N(C(C(=O)OCc2ccc([N+](=O)[O-])cc2)=P(c2ccccc2)(c2ccccc2)c2ccccc2)[C@@H]1SC(C)=O

HCID56625245

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6344

Dichloromethane

CH2Cl2

溶剂HCID8028

Tetrahydrofuran

C4H8O

PROCEDURE

实验过程

0.84 g of triphenylphosphine is added to a solution of 0.63 g of 2-[(3S,4R)-4-acetylthio-3-methoxy-2-oxoazetidin-1-yl]-2-chloroacetic acid p-nitrobenzyl ester in 1.8 ml of dry tetrahydrofuran, and the mixture is stirred overnight at room temperature under nitrogen. The mixture is diluted with methylene chloride and washed with a cold, saturated, aqueous sodium bicarbonate solution. Additional washing with water, drying over sodium sulphate and concentrating by evaporation in vacuo yield the crude title compound which is purified by chromatography over silica gel with toluene/ethyl acetate (19:1 to 3:1).

WORKUP

后处理

washwashed with a cold, saturated, aqueous sodium bicarbonate solution
washAdditional washing with water
dry with materialdrying over sodium sulphate
concentrationconcentrating by evaporation in vacuo

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-675c263f952a46668f5762e7b39883ef
来源数据集: uspto-grants-1987_09
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04692442
来源说明: uspto-grants-1987_09

反应 SMILES

[C:1]1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:20]([C:23]1[CH:45]=[CH:44][C:26]([CH2:27][O:28][C:29](=[O:43])[CH:30]([N:32]2[C@H:35]([S:36][C:37](=[O:39])[CH3:38])[C@@H:34]([O:40][CH3:41])[C:33]2=[O:42])Cl)=[CH:25][CH:24]=1)([O-:22])=[O:21]>O1CCCC1.C(Cl)Cl>[N+:20]([C:23]1[CH:45]=[CH:44][C:26]([CH2:27][O:28][C:29](=[O:43])[C:30]([N:32]2[C@H:35]([S:36][C:37](=[O:39])[CH3:38])[C@@H:34]([O:40][CH3:41])[C:33]2=[O:42])=[P:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:25][CH:24]=1)([O-:22])=[O:21]