HRID21710

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID313

Hydrochloric Acid

ClH

HCID516892

Sodium Bicarbonate

CHNaO3

结构：COc1ccc(COC(=O)[C@H](C)[C@@H]2[C@@H]([C@@H](C)O[Si](C)(C)C(C)(C)C)C(=O)N2CC(=O)OCc2ccc([N+](=O)[O-])cc2)cc1

HCID15223718

未命名化合物

PRODUCTS

生成物

结构：C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1C(=O)N(CC(=O)OCc2ccc([N+](=O)[O-])cc2)[C@@H]1[C@@H](C)C(=O)O

HCID15223720

未命名化合物

结构：C[C@@H](O)[C@H]1C(=O)N(CC(=O)OCc2ccc([N+](=O)[O-])cc2)[C@@H]1[C@@H](C)C(=O)O

HCID15223722

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6344

Dichloromethane

CH2Cl2

PROCEDURE

实验过程

To a solution of (3S,4S)-3-[(1R)-1-t-butyldimethylsilyloxyethyl]-4-[(1R)-1-p-methoxybenzyloxycarbonylethyl]-1-(p-nitrobenzyloxycarbonylmethyl)azetidin-2-one (142 mg) in dry methylene chloride, there was BF3 -Et2O complex (163 mg) under ice-cooling, followed by stirring at room temperature. The reaction mixture was poured into a cold aqueous sodium bicarbonate solution, acidified with dilute hydrochloric acid and extracted with ethyl acetate three times. The organic layer was washed successively with dilute hydrochloric acid and brine, dried over sodium sulfate and evaporated. The residue was purified by silica gel chromatography to give (3S,4S)-3-[(1R)-1-t-butyldimethylsilyloxyethyl]-4-[(1R)-1-carboxyethyl]-1-(p-nitrobenzyloxycarbonylmethyl)azetidin-2-one (Compound A) and (3S,4S)-3-[(1R)-1-hydroxyethyl]-4-[(1R)-1-carboxyethyl]-1-(p-nitrobenzyloxycarbonylmethyl)azetidin-2-one (Compound B).

WORKUP

后处理

temperaturecooling
extractionextracted with ethyl acetate three times
washThe organic layer was washed successively with dilute hydrochloric acid and brine
dry with materialdried over sodium sulfate
customevaporated
customThe residue was purified by silica gel chromatography

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-35ee0b6820d247ea9c22f7c042504b9a
来源数据集: uspto-grants-1995_06
DOI: 10.6084/m9.figshare.5104873.v1
专利: US05424422
来源说明: uspto-grants-1995_06

反应 SMILES

[Si:1]([O:8][C@@H:9]([C@@H:11]1[C@@H:14]([C@H:15]([C:17]([O:19]CC2C=CC(OC)=CC=2)=[O:18])[CH3:16])[N:13]([CH2:29][C:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][C:37]([N+:40]([O-:42])=[O:41])=[CH:36][CH:35]=2)=[O:31])[C:12]1=[O:43])[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(=O)(O)[O-].[Na+].Cl>C(Cl)Cl>[Si:1]([O:8][C@@H:9]([C@@H:11]1[C@@H:14]([C@H:15]([C:17]([OH:19])=[O:18])[CH3:16])[N:13]([CH2:29][C:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][C:37]([N+:40]([O-:42])=[O:41])=[CH:36][CH:35]=2)=[O:31])[C:12]1=[O:43])[CH3:10])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2].[OH:8][C@@H:9]([C@@H:11]1[C@@H:14]([C@H:15]([C:17]([OH:19])=[O:18])[CH3:16])[N:13]([CH2:29][C:30]([O:32][CH2:33][C:34]2[CH:35]=[CH:36][C:37]([N+:40]([O-:42])=[O:41])=[CH:38][CH:39]=2)=[O:31])[C:12]1=[O:43])[CH3:10]