HRID2173760

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID11430

Potassium Carbonate

CK2O3

结构：CC(C)(C)OC(=O)CCN(CCOS(C)(=O)=O)S(=O)(=O)c1ccccc1[N+](=O)[O-]

HCID87121174

未命名化合物

HCID178469316

未命名化合物

PRODUCTS

生成物

结构：CCOC(=O)c1cc(OCCN(CCC(=O)OC(C)(C)C)S(=O)(=O)c2ccccc2[N+](=O)[O-])cc(C(=O)OCC)n1

HCID66714132

未命名化合物

收率 47%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

CONDITIONS

反应条件

温度: 60 °C

PROCEDURE

实验过程

To a solution of 10.6 g of tert-butyl 3-[(2-methanesulfonyloxy-ethyl)-(2-nitro-benzenesulfonyl)-amino]-propionate in 220 ml of DMF was added 16.2 g of K2CO3 and 5.6 g of diethyl 4-hydroxy-pyridine-2,6-dicarboxylate. The mixture was heated for 20 hours at 60° C. and then concentrated under reduced pressure and taken up in 200 ml of water and 200 ml of EtOAc. The aqueous phase was extracted 2× with EtOAc. The organic phases were combined, washed with saturated NaCl solution, dried over MgSO4, concentrated under reduced pressure and purified by flash chromatography on silica (Merck EasyVarioPrep 600 g column, Si60 15-40 μm), using a gradient of 0 to 20% EtOAc in DCM. The fractions containing the desired product were combined and concentrated under reduced pressure. 6.56 g of diethyl 4-{2-[(2-tert-butoxycarbonyl-ethyl)-(2-nitro-benzenesulfonyl)-amino]-ethoxy}-pyridine-2,6-dicarboxylate were obtained. LC/MS (C): tr=4.14 min; [M+H]+: m/z 596.

WORKUP

后处理

concentrationconcentrated under reduced pressure
extractionThe aqueous phase was extracted 2× with EtOAc
washwashed with saturated NaCl solution
dry with materialdried over MgSO4
concentrationconcentrated under reduced pressure
custompurified by flash chromatography on silica (Merck EasyVarioPrep 600 g column, Si60 15-40 μm)
additionThe fractions containing the desired product
concentrationconcentrated under reduced pressure

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-c187d0fcda0f42b085f9f00d12f64588
来源数据集: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
专利: US09056914B2
来源说明: uspto-grants-2015_06

反应 SMILES

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