HRID41532

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID313

Hydrochloric Acid

ClH

HCID14798

Sodium Hydroxide

HNaO

$结构：CCCCCC[C@H](OC)c1cccc(-c2csc(NC(=O)c3cc(Cl)c(/C=C(\C)C(=O)OCC)c(Cl)c3)n2)c1OC$

HCID59544888

未命名化合物

PRODUCTS

生成物

$结构：CCCCCC[C@H](OC)c1cccc(-c2csc(NC(=O)c3cc(Cl)c(/C=C(\C)C(=O)O)c(Cl)c3)n2)c1OC$

HCID59544885

未命名化合物

收率 89.9%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID702

Ethanol

C2H6O

溶剂HCID8028

Tetrahydrofuran

C4H8O

PROCEDURE

实验过程

Ethyl (S)-(E)-3-(2,6-dichloro-4-(4-(2-methyloxy-3-(1-methyloxyheptyl)phenyl)thiazol-2-ylcarbamoyl)phenyl)-2-methylacrylate (14, 6.76 g) obtained in the fifth step was dissolved in THF (20 mL) and ethanol (20 mL), a 4 mol/L sodium hydroxide aqueous solution (13.5 mL) was added, and the mixture was stirred at room temperature for 2 hours. The reaction solution was neutralized with hydrochloric acid, and extracted with ethyl acetate. The extraction residue was recrystallized with methanol to obtain (S)-(E)-3-(2,6-dichloro-4-(4-(2-methyloxy-3-(1-methyloxyheptyl)phenyl)thiazol-2-ylcarbamoyl)phenyl)-2-methylacrylic acid (C-1B, 5.8 g, yield 88%).

WORKUP

后处理

extractionextracted with ethyl acetate
customThe extraction residue was recrystallized with methanol

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-0ee5c6ebea7c4fda94cf29306b7654b1
来源数据集: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08530668B2
来源说明: uspto-grants-2013_09

反应 SMILES

[Cl:1][C:2]1[CH:7]=[C:6]([C:8](=[O:32])[NH:9][C:10]2[S:11][CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C@@H:21]([O:28][CH3:29])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:16]=3[O:30][CH3:31])[N:14]=2)[CH:5]=[C:4]([Cl:33])[C:3]=1/[CH:34]=[C:35](\[CH3:41])/[C:36]([O:38]CC)=[O:37].[OH-].[Na+].Cl>C1COCC1.C(O)C>[Cl:33][C:4]1[CH:5]=[C:6]([C:8](=[O:32])[NH:9][C:10]2[S:11][CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C@@H:21]([O:28][CH3:29])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:16]=3[O:30][CH3:31])[N:14]=2)[CH:7]=[C:2]([Cl:1])[C:3]=1/[CH:34]=[C:35](\[CH3:41])/[C:36]([OH:38])=[O:37]