HRID376586

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID243

Benzoic acid

C7H6O2

结构：CCCCP(CCCC)(CCCC)=C(C(=O)OCc1ccc(OC)cc1)N1C(=O)[C@@H](NC(=O)COc2ccccc2)[C@H]1SCC(=O)C1CCC(COC)O1

HCID88237107

未命名化合物

PRODUCTS

生成物

结构：COCC1CCC(C2=C(C(=O)OCc3ccc(OC)cc3)N3C(=O)[C@@H](NC(=O)COc4ccccc4)[C@H]3SC2)O1

HCID131721506

未命名化合物

收率 62.8%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID1140

Toluene

C7H8

PROCEDURE

实验过程

A solution of 4-methoxybenzyl 2-[(3R,4R)-4-[(2RS,5SR)-5-methoxymethyltetrahydrofuran-2-ylcarbonylmethylthio]-3-phenoxyacetamidoazetidin-2-on-1-yl]-2-tri-n-butylphosphoranylideneacetate (4.25g) and benzoic acid (20mg) in toluene (100ml) was heated to reflux for 10h. The mixture was cooled and the solvent evaporated. The product (1.93g) was isolated by column chromatography of the residue using gradient elution (silica gel 1:1 hexane : ethyl acetate going to neat ethyl acetate); vmax (CHCl3) 3409, 1784, 1722 and 1695cm-1.

WORKUP

后处理

temperatureto reflux for 10h
temperatureThe mixture was cooled
customthe solvent evaporated

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-254adb1d542048d888026e2e6d8f3955
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

[CH3:1][O:2][CH2:3][CH:4]1[O:8][CH:7]([C:9]([CH2:11][S:12][C@H:13]2[N:16]([C:17](=P(CCCC)(CCCC)CCCC)[C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=3)=[O:19])[C:15](=[O:43])[C@H:14]2[NH:44][C:45](=[O:54])[CH2:46][O:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)=O)[CH2:6][CH2:5]1.C(O)(=O)C1C=CC=CC=1>C1(C)C=CC=CC=1>[CH3:1][O:2][CH2:3][CH:4]1[O:8][CH:7]([C:9]2[CH2:11][S:12][C@@H:13]3[C@H:14]([NH:44][C:45](=[O:54])[CH2:46][O:47][C:48]4[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=4)[C:15](=[O:43])[N:16]3[C:17]=2[C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)=[O:19])[CH2:6][CH2:5]1