HRID926059

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID311

Citric Acid

C6H8O7

HCID6340

Ethane, iodo-

C2H5I

HCID11430

Potassium Carbonate

CK2O3

反应SMILES：CCOC(=O)CCCNS(=O)(=O)c1cccc(C(=O)Nc2sc3c(c2C(=O)Nc2ccc(CCc4ccc(C(=O)OC)cc4)cc2)CCCC3)c1

HCID68207789

未命名化合物

PRODUCTS

产物

反应SMILES：CCOC(=O)CCCN(CC)S(=O)(=O)c1cccc(C(=O)Nc2sc3c(c2C(=O)Nc2ccc(CCc4ccc(C(=O)OC)cc4)cc2)CCCC3)c1

HCID71238217

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6228

Dimethylformamide

C3H7NO

CONDITIONS

反应条件

温度: 60 °C

PROCEDURE

实验过程

A mixture of 200 mg of methyl 4-{2-[4-({[2-({3-[(4-ethoxy-4-oxobutyl)sulfamoyl]benzoyl}amino)-4,5,6,7-tetrahydro-1-benzothiophen-3-yl]carbonyl}amino)phenyl]ethyl}benzoate, 0.059 mL of ethyl iodide, 113 mg of potassium carbonate, and 2.0 mL of DMF was stirred at 60° C. overnight. To the reaction mixture was added an aqueous citric acid solution, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine in this order, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-chloroform) to obtain 137 mg of methyl 4-{2-[4-({[2-({3-[(4-ethoxy-4-oxobutyl)(ethyl)sulfamoyl]benzoyl}amino)-4,5,6,7-tetrahydro-1-benzothiophen-3-yl]carbonyl}amino)phenyl]ethyl}benzoate as a yellow solid.

WORKUP

后处理

extractionfollowed by extraction with ethyl acetate
washThe organic layer was washed with water and saturated brine in this order
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (hexane-chloroform)

来源与证据

来源类型: Open Reaction Database
ORD记录: ord-9a42d670dde14174b1c69bc950722ef3
来源数据集: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
专利号: US09284295B2
来源说明: uspto-grants-2016_03

反应SMILES

[CH2:1]([O:3][C:4](=[O:51])[CH2:5][CH2:6][CH2:7][NH:8][S:9]([C:12]1[CH:13]=[C:14]([CH:48]=[CH:49][CH:50]=1)[C:15]([NH:17][C:18]1[S:19][C:20]2[CH2:47][CH2:46][CH2:45][CH2:44][C:21]=2[C:22]=1[C:23]([NH:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][C:34]2[CH:43]=[CH:42][C:37]([C:38]([O:40][CH3:41])=[O:39])=[CH:36][CH:35]=2)=[CH:28][CH:27]=1)=[O:24])=[O:16])(=[O:11])=[O:10])[CH3:2].[CH2:52](I)[CH3:53].C(=O)([O-])[O-].[K+].[K+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:51])[CH2:5][CH2:6][CH2:7][N:8]([CH2:52][CH3:53])[S:9]([C:12]1[CH:13]=[C:14]([CH:48]=[CH:49][CH:50]=1)[C:15]([NH:17][C:18]1[S:19][C:20]2[CH2:47][CH2:46][CH2:45][CH2:44][C:21]=2[C:22]=1[C:23]([NH:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][C:34]2[CH:43]=[CH:42][C:37]([C:38]([O:40][CH3:41])=[O:39])=[CH:36][CH:35]=2)=[CH:28][CH:27]=1)=[O:24])=[O:16])(=[O:11])=[O:10])[CH3:2]