HRID376585

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID962

Water

H2O

HCID8471

Triethylamine

C6H15N

HCID10867196

Acetic acid, oxo-, (4-methoxyphenyl)methyl ester

C10H10O4

结构：COCC1CCC(C(=O)CS[C@H]2NC(=O)[C@H]2NC(=O)COc2ccccc2)O1

HCID70256441

未命名化合物

PRODUCTS

生成物

结构：COCC1CCC(C(=O)CS[C@@H]2[C@H](NC(=O)COc3ccccc3)C(=O)N2C(O)C(=O)OCc2ccc(OC)cc2)O1

HCID131721504

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6212

Chloroform

CHCl3

溶剂HCID6365

1,1-Dichloroethane

C2H4Cl2

2 次

PROCEDURE

实验过程

A solution of 4-methoxybenzyl glyoxylate (1.82g) in dichloroethane (30ml) was heated at reflux using a Dean and Stark water separator for 1h. The solution was then cooled to room temperature and then (3R,4R)-4-[(2RS,5SR)-5-methoxymethyltetrahydrofuran-2-ylcarbonylmethylthio]-3-phenoxyacetamidoazetidin-2-one (2.94g) in dichloroethane (20ml) was added followed by triethylamine (0.1ml). The mixture was stirred at room temperature for 1h and then the solvents were removed on a rotary evaporator. The product was isolated as a mixture of isomers (3.23g) by column chromatography of the residue (silica gel, ethyl acetate as eluent); vmax (CHCl3) 3411, 1780, 1745 and 1691cm-1.

WORKUP

后处理

temperatureat reflux
customthe solvents were removed on a rotary evaporator
customThe product was isolated as a mixture of isomers (3.23g) by column chromatography of the residue (silica gel, ethyl acetate as eluent)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-ac794374cc484f27bfe737236af01091
来源数据集: uspto-grants-2000_02
DOI: 10.6084/m9.figshare.5104873.v1
专利: US06020329
来源说明: uspto-grants-2000_02

反应 SMILES

[C:1]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)(=[O:4])[CH:2]=[O:3].O.[CH3:16][O:17][CH2:18][CH:19]1[O:23][CH:22]([C:24]([CH2:26][S:27][C@H:28]2[NH:31][C:30](=[O:32])[C@H:29]2[NH:33][C:34](=[O:43])[CH2:35][O:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[O:25])[CH2:21][CH2:20]1.C(N(CC)CC)C>ClC(Cl)C.C(Cl)(Cl)Cl>[OH:3][CH:2]([N:31]1[C@H:28]([S:27][CH2:26][C:24]([CH:22]2[CH2:21][CH2:20][CH:19]([CH2:18][O:17][CH3:16])[O:23]2)=[O:25])[C@H:29]([NH:33][C:34](=[O:43])[CH2:35][O:36][C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:30]1=[O:32])[C:1]([O:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH3:14])=[CH:11][CH:12]=1)=[O:4]