HRID1464733

反应详情

EQUATION

反应方程式

REACTANTS

反应物

结构：C=CCOC(=O)N1C[C@@H](S)C[C@H]1C(=O)N(C)C

HCID10083864

未命名化合物

结构：C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1C(=O)N[C@@H]1[C@@H](C)C(=S)Sc1ccccc1

HCID22851409

未命名化合物

PRODUCTS

生成物

结构：C=CCOC(=O)N1C[C@@H](SC(=S)[C@H](C)[C@H]2NC(=O)[C@@H]2[C@@H](C)O[Si](C)(C)C(C)(C)C)C[C@H]1C(=O)N(C)C

HCID22851410

未命名化合物

收率 77.1%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6342

Acetonitrile

C2H3N

PROCEDURE

实验过程

To a mixture of (3S,4S)-3-[(1R)-1-(tertbutyldimethylsilyloxy)ethyl]-4-[(1R)-1-{(phenylthio)thiocarbonyl}ethyl]-2-oxoazetidine (100 mg) and cuprous chloride (30 mg) in acetonitrile (1 ml) was added (2S,4S)-1-allyloxycarbonyl-2-(dimethylcarbamoyl)-4-mercaptopyrrolidine (130 mg) and the mixture was stirred at the ambient temperature for 5 hours. The mixture was purified by preparative thin layer chromatography (developed with ethyl acetate) to give (3S,4S)-4-[(1R)-1-{((2S,4S)-1-allyloxycarbonyl-2-(dimethylcarbamoyl)pyrrolidin- 4-ylthio)thiocarbonyl}ethyl]-3-[(1R)-1-(tertbutyldimethylsilyloxy)ethyl]-2-oxoazetidine (105 mg).

WORKUP

后处理

customThe mixture was purified by preparative thin layer chromatography (developed with ethyl acetate)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-43e83161d441404fac44f5e2dc50e56e
来源数据集: uspto-grants-1994_04
DOI: 10.6084/m9.figshare.5104873.v1
专利: US05306816
来源说明: uspto-grants-1994_04

反应 SMILES

[C:1]([Si:5]([CH3:26])([CH3:25])[O:6][C@@H:7]([C@@H:9]1[C@@H:12]([C@H:13]([C:15](SC2C=CC=CC=2)=[S:16])[CH3:14])[NH:11][C:10]1=[O:24])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[CH2:27]([O:30][C:31]([N:33]1[CH2:37][C@@H:36]([SH:38])[CH2:35][C@H:34]1[C:39](=[O:43])[N:40]([CH3:42])[CH3:41])=[O:32])[CH:28]=[CH2:29]>C(#N)C>[CH2:27]([O:30][C:31]([N:33]1[CH2:37][C@@H:36]([S:38][C:15]([C@@H:13]([C@H:12]2[NH:11][C:10](=[O:24])[C@@H:9]2[C@H:7]([O:6][Si:5]([C:1]([CH3:3])([CH3:2])[CH3:4])([CH3:25])[CH3:26])[CH3:8])[CH3:14])=[S:16])[CH2:35][C@H:34]1[C:39](=[O:43])[N:40]([CH3:41])[CH3:42])=[O:32])[CH:28]=[CH2:29]