HRID279686

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID11430

Potassium Carbonate

CK2O3

HCID9816147

Ethyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoate

C13H18O4

结构：CC(C)(C)OC(=O)Nc1ccc(CCCS(=O)(=O)[O-])cc1

HCID22988767

未命名化合物

PRODUCTS

生成物

结构：CCOC(=O)[C@H](Cc1ccc(OCCc2ccc(NC(=O)OC(C)(C)C)cc2)cc1)OCC

HCID11812512

未命名化合物

收率 99,648.797%

AUXILIARIES

试剂、催化剂与溶剂

催化剂HCID22988767

未命名化合物

溶剂HCID6342

Acetonitrile

C2H3N

PROCEDURE

实验过程

2-[4-(tert-Butoxycarbonylamino)phenyl]ethylmethanesulfonate (52.9 g; 0.168 mmole), (S)-2-ethoxy-3-(4-hydroxyphenyl)propanoic acid ethyl ester (40 g; 0.168 mmole) and potassium carbonate (69.5 g; 0.503 mmole) were mixed in acetonitrile (1200 ml) and refluxed overnight. Another portion of 2-[4-(tert-butoxycarbonylamino)phenyl]-ethylmethanesulfonate (2.5 g; 7.9 mmole) was added. The reaction mixture was refluxed for 8 more hours then filtered. Evaporation of the filtrate gave 76.6 g 3-{4-[2-(4-tert-butoxycarbonylaminophenyl)ethoxy]phenyl}-(S)-2-ethoxypropanoic acid ethyl ester.

WORKUP

后处理

temperaturerefluxed overnight
temperatureThe reaction mixture was refluxed for 8 more hours
filtrationthen filtered
customEvaporation of the filtrate

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-3dac91c56d5e4e2fb02441adc15e8e15
来源数据集: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
专利: US06362360B1
来源说明: uspto-grants-2002_03

反应 SMILES

[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16]CS([O-])(=O)=O)=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:22]([O:24][C:25](=[O:38])[C@@H:26]([O:35][CH2:36][CH3:37])[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=1)[CH3:23].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C(OC(NC1C=CC(CCCS([O-])(=O)=O)=CC=1)=O)(C)(C)C>[CH2:22]([O:24][C:25](=[O:38])[C@@H:26]([O:35][CH2:36][CH3:37])[CH2:27][C:28]1[CH:29]=[CH:30][C:31]([O:34][CH2:16][CH2:15][C:12]2[CH:11]=[CH:10][C:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[CH:14][CH:13]=2)=[CH:32][CH:33]=1)[CH3:23]