海萝胶 → N-(2-ethoxycarbonyloxy-4-methoxybenzoyl)cysteamine

HRID 465916

反应方程式

HRID 465916 反应方程式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:12])[C:6](=[CH:10][CH:11]=1)[C:7]([OH:9])=O.[C:13](Cl)(=[O:17])[O:14][CH2:15][CH3:16].[NH2:19][CH2:20][CH2:21][SH:22].Cl>C(Cl)Cl.C(N(CC)CC)C>[CH2:15]([O:14][C:13]([O:12][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:11]=[CH:10][C:6]=1[C:7]([NH:19][CH2:20][CH2:21][SH:22])=[O:9])=[O:17])[CH3:16]

参与物

7

反应物 4

HCID 313海萝胶HCID 6058巯基乙胺HCID 10928氯甲酸乙酯HCID 752314-甲氧基水杨酸

产物 1

HCID 14719509N-(2-ethoxycarbonyloxy-4-methoxybenzoyl)cysteamine收率 89%

试剂、催化剂与溶剂 2

HCID 6344二氯甲烷溶剂2 次HCID 8471三乙胺溶剂

反应条件

温度
-15 °C

实验过程

Under argon atmosphere, 2.84 g of 4-methoxysalicylic acid was dispersed in 45 ml of methylene chloride, and the dispersion was cooled to -15° C. To the dispersion was added 3.76 g of triethylamine and 3.77 g of ethyl chlorocarbonate, and the mixture was agitated for 1.5 hour. To the mixture was added a solution of 1.56 g of cysteamine in 5 ml of methylene chloride, and the mixture was agitated at -15° C. for 2 hours. The reaction mixture was poured into 1N aqueous hydrochloric acid, and extracted with methylene chloride. The organic layer was washed with saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. The solvent was distilled off in evacuated atomosphere, and the residue was subjected to column chromatography using silica gel. There was obtained 4.50 g of N-(2-ethoxycarbonyloxy-4-methoxybenzoyl)cysteamine.

后处理

  1. stirringthe mixture was agitated at -15° C. for 2 hours
  2. extractionextracted with methylene chloride
  3. washThe organic layer was washed with saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off in evacuated atomosphere

来源与证据

ORD记录
ord-3ae318039fa6472396b71c8f4c0654bb
来源数据集
uspto-grants-1992_10
专利号
US05155106

关联笔记

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