HRID462402

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID11776

Triphenylphosphine

C18H15P

结构：CC(=O)S[C@@H]1CC(=O)N1C(Cl)C(=O)OCc1ccc([N+](=O)[O-])cc1

HCID53951525

未命名化合物

PRODUCTS

生成物

结构：CC(=O)S[C@@H]1CC(=O)N1C(C(=O)OCc1ccc([N+](=O)[O-])cc1)=P(c1ccccc1)(c1ccccc1)c1ccccc1

HCID18597904

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID31275

1,4-Dioxane

C4H8O2

PROCEDURE

实验过程

3.144 g (~1.5 equivalents) of triphenylphosphine and 12 g of poly-Hunig base are added to a solution of 3.1 g of 2-[(4R)-4-acetylthio-2-oxoazetidin-1-yl]-2-chloroacetic acid p-nitrobenzyl ester in 120 ml of dioxan and the mixture is stirred for 17 hours at 50° under nitrogen. The poly-Hunig base is filtered off, washed with dioxan and the filtrate concentrated in vacuo. The residue is chromatographed twice over silica gel with toluene and toluene/ethyl acetate (4:1 and 3:2) and yields the title compound.

WORKUP

后处理

filtrationThe poly-Hunig base is filtered off
washwashed with dioxan
concentrationthe filtrate concentrated in vacuo
customThe residue is chromatographed twice over silica gel with toluene and toluene/ethyl acetate (4:1 and 3:2)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-36a129eec9ef4383924630abf9eb194f
来源数据集: uspto-grants-1985_05
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04515717
来源说明: uspto-grants-1985_05

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:43]=[CH:42][C:26]([CH2:27][O:28][C:29](=[O:41])[CH:30]([N:32]2[C@H:35]([S:36][C:37](=[O:39])[CH3:38])[CH2:34][C:33]2=[O:40])Cl)=[CH:25][CH:24]=1)([O-:22])=[O:21]>O1CCOCC1>[N+:20]([C:23]1[CH:24]=[CH:25][C:26]([CH2:27][O:28][C:29](=[O:41])[C:30]([N:32]2[C@H:35]([S:36][C:37](=[O:39])[CH3:38])[CH2:34][C:33]2=[O:40])=[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:42][CH:43]=1)([O-:22])=[O:21]