HRID862396

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID15005996

未命名化合物

结构：COC=CC(=O)C[C@H]1NC(=O)[C@@H]1[C@@H](C)O[Si](C)(C)C(C)(C)C

HCID67627134

未命名化合物

PRODUCTS

生成物

结构：COC=CC(=O)C[C@@H]1[C@@H]([C@@H](C)O[Si](C)(C)C(C)(C)C)C(=O)N1C(O)C(=O)OCc1ccc(OC)cc1

HCID67755989

未命名化合物

收率 93%

AUXILIARIES

试剂、催化剂与溶剂

催化剂HCID8471

Triethylamine

C6H15N

溶剂HCID241

Benzene

C6H6

PROCEDURE

实验过程

A mixture of (3S ,4R) 3-((1R)-1-(tert-butyldimethylsilyloxy)ethyl)-4-(4-methoxy-2-oxobut-3-en-1-yl)azetidin-2-one (100 mg, 0.3 mM), 4-methoxybenzyl dihydroxyacetate (72 mg, 0.33 mM) and 2 drops of triethylamine in benzene (5 ml) was heated at reflux for 1 hour. The solvent was evaporated and the product purified by subjecting to chromatography on silica, eluting with ether to give 4-methoxybenzyl 2-[(3S,4R)-3-[(1R)-1-(tert-butyldimethylsilyloxy)-ethyl]-4-[4-methoxy-2-oxobut-3-en-1-yl]-2-azetidinone-1-yl]-2-hydroxy-acetate (147 mg, 93%). IR (film, NaCl) 3310, 1745.

WORKUP

后处理

temperaturewas heated
temperatureat reflux for 1 hour
customThe solvent was evaporated
customthe product purified
washeluting with ether

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-269deb59150e47869406382a87865ab3
来源数据集: uspto-grants-1998_02
DOI: 10.6084/m9.figshare.5104873.v1
专利: US05719139
来源说明: uspto-grants-1998_02

反应 SMILES

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