HRID1970027

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID69015

Sulfuric acid, dipropyl ester

C6H14O4S

结构：O=C(O)c1c[nH]c2c(=O)[nH]c3ccc(S(=O)(=O)Cl)cc3c12

HCID45121068

未命名化合物

HCID66569218

未命名化合物

PRODUCTS

生成物

结构：CC(C)(C)OC(=O)N1CCC[C@H]1CN(C1CC1)S(=O)(=O)c1ccc2[nH]c(=O)c3[nH]ccc3c2c1.CCCC(=O)[O-]

HCID86627532

未命名化合物

PROCEDURE

实验过程

(S)-8-[(1-tert-butoxycarbony-pyrrolidin-2-ylmethyl)-cyclopropyl-sulfamoyl]-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-propyl carboxylate is prepared according to synthesis 111, from 326 mg (1 mmol) of 8-chlorosulfonyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid and 288 mg (1.2 mmol) of (S)-1-tert-butoxycarbonyl-2-cyclopropylaminomethyl-pyrrolidine to give, after esterification according to general method C (using di-n-propylsulfate as the dialkylsulfate) and purification by chromatography on silica (eluent dichloromethane/methanol 99/1 then 95/5), 99 mg (17% in two stages) of (S)-8-[(1-tert-butoxycarbonyl-pyrrolidin-2-ylmethyl)-cyclopropyl-sulfamoyl]-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-propyl carboxylate in the form of a white solid.

WORKUP

后处理

customto give
custompurification by chromatography on silica (eluent dichloromethane/methanol 99/1

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-7e5ace70b1614b70be0996cd24e7e9ec
来源数据集: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08426437B2
来源说明: uspto-grants-2013_04

反应 SMILES

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