HRID1578893

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID962

Water

H2O

HCID70205

Methyl oxoacetate

C3H4O3

结构：O=C1NC(SCC#Cc2ccccc2)C1NC(c1ccccc1)(c1ccccc1)c1ccccc1

HCID21519177

未命名化合物

PRODUCTS

生成物

结构：COC(=O)C(O)N1C(=O)C(NC(c2ccccc2)(c2ccccc2)c2ccccc2)C1SCC#Cc1ccccc1

HCID53714964

未命名化合物

收率 64%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID241

Benzene

C6H6

PROCEDURE

实验过程

3-(Triphenylmethylamino)-4-(3-phenylprop-2-ynylthio) azetidin-2-one (526mg) and methyl glyoxylate (1.17g) were refluxed in dry benzene (25ml) with provision for the removal of water. After 11/2 hours the solvent was evaporated and the residue was chromatographed on silica to give 1-(1-hydroxy-1-methoxycarbonylmethyl)-3-(triphenyl methylamino)-4-(3-phenylprop-2-ynylthio)azetidin-2-one as an amorphous solid (399 mg). νmax (CHCl3) 3475 (--OH), 1770 (β-lactam), 1750 (ester) cm-1.

WORKUP

后处理

customAfter 11/2 hours the solvent was evaporated
customthe residue was chromatographed on silica

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-3cc90c8cd3aa4749b64a735c745c1059
来源数据集: uspto-grants-1976_02
DOI: 10.6084/m9.figshare.5104873.v1
专利: US03939157
来源说明: uspto-grants-1976_02

反应 SMILES

[C:1]1([C:7]([NH:20][CH:21]2[CH:24]([S:25][CH2:26][C:27]#[C:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[NH:23][C:22]2=[O:35])([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.[C:36]([O:40][CH3:41])(=[O:39])[CH:37]=[O:38].O>C1C=CC=CC=1>[OH:38][CH:37]([N:23]1[CH:24]([S:25][CH2:26][C:27]#[C:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:21]([NH:20][C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:22]1=[O:35])[C:36]([O:40][CH3:41])=[O:39]