HRID1789840

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID8471

Triethylamine

C6H15N

HCID8857

Ethyl acetate

C4H8O2

结构：C=C(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)cc1C)C(=O)OCC

HCID53943554

未命名化合物

HCID178418634

未命名化合物

PRODUCTS

生成物

结构：CCOC(=O)C(CSC(C)=O)Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c(C)c1

HCID54221100

未命名化合物

收率 21%

结构：CCOC(=O)C(CSC(C)=O)Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)cc1C

HCID57094567

未命名化合物

PROCEDURE

实验过程

Triethylamine (0.279 mL, 2.0 mmol) was added to a solution of 2-(6-[N,N-bis(tert-butoxycarbonyl)amino]-4-methyl-pyridin-3-ylmethyl)-acrylic acid ethyl ester (0.8 g, 1.9 mmol) in thioacetic acid (3 mL) at 0° C. The mixture was stirred at room temperature for 16 h. Ethyl acetate was added and the organic phase was washed with water, saturated NaHCO3 and brine and dried. The crude product was purified by flash chromatography (toluene/ethyl acetate, 3:1→1:2) to give pure 2-acetylsulfanylmethyl-3-(6-[N,N-bis(tert-butoxycarbonyl)amino]-5-methyl-pyridin-3-yl)-propionic acid ethyl ester (200 mg, 21%) and slightly impure 2-acetylsulfanylmethyl-3-(6-[N,N-bis(tert-butoxycarbonyl)amino]-4-methyl-pyridin-3-yl)-propionic acid ethyl ester (0.68 g).

WORKUP

后处理

washthe organic phase was washed with water, saturated NaHCO3 and brine
customdried
customThe crude product was purified by flash chromatography (toluene/ethyl acetate, 3:1→1:2)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-85be6c3d5cf947ad8578ebfa34a63d26
来源数据集: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07071175B1
来源说明: uspto-grants-2006_07

反应 SMILES

[CH2:1](N(CC)CC)C.[CH2:8]([O:10][C:11](=[O:37])[C:12]([CH2:14][C:15]1[CH:16]=[N:17][C:18]([N:22]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[CH:19][C:20]=1[CH3:21])=[CH2:13])[CH3:9].C(OCC)(=O)C.[C:44]([OH:47])(=[S:46])[CH3:45]>>[CH2:8]([O:10][C:11](=[O:37])[CH:12]([CH2:13][S:46][C:44](=[O:47])[CH3:45])[CH2:14][C:15]1[CH:16]=[N:17][C:18]([N:22]([C:30]([O:32][C:33]([CH3:36])([CH3:34])[CH3:35])=[O:31])[C:23]([O:25][C:26]([CH3:28])([CH3:29])[CH3:27])=[O:24])=[C:19]([CH3:1])[CH:20]=1)[CH3:9].[CH2:8]([O:10][C:11](=[O:37])[CH:12]([CH2:13][S:46][C:44](=[O:47])[CH3:45])[CH2:14][C:15]1[CH:16]=[N:17][C:18]([N:22]([C:23]([O:25][C:26]([CH3:29])([CH3:27])[CH3:28])=[O:24])[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[CH:19][C:20]=1[CH3:21])[CH3:9]