反应 #2171064

ord-c5162c4ad99a426eb20a5acafc0de362

反应方程式

CCOC(C)=O
ethyl acetate
O=S(=O)(O)O
sulfuric acid
CCOC(CN1C(=O)C(CC(=O)Nc2ccc(C)cc2)(NC(=O)Nc2ccc(CO[Si](C)(C)C(C)(C)C)cc2)c2ccccc21)OCC
3-(N′-(4-t-butyldimethylsilyloxymethylphenyl)ureido)-1-(2,2-diethoxyethyl)-3-((4-methylphenyl)aminocarbonylmethyl) indolin-2-one
O
Water
CCOC(CN1C(=O)C(CC(=O)Nc2ccc(C)cc2)(NC(=O)Nc2ccc(CO)cc2)c2ccccc21)OCC
title compound
收率 88.0%
CCOC(CN1C(=O)C(CC(=O)Nc2ccc(C)cc2)(NC(=O)Nc2ccc(CO)cc2)c2ccccc21)OCC
1-(2,2-diethoxyethyl)-3-(N′-(4-hydroxymethylphenyl)ureido)-3-((4-methylphenyl)aminocarbonylmethyl)indolin-2-one
收率 88.0%

溶剂

反应条件

温度
22.5°CELSIUS
详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    干燥the organic layer was dried with anhydrous sodium hydrogensulfate
  2. 2
    workup.DISTILLATIONthe solvent was distilled off
  3. 3
    其他The reaction mixture was purified by silica gel column chromatography

实验过程

3-(N′-(4-t-butyldimethylsilyloxymethylphenyl)ureido)-1-(2,2-diethoxyethyl)-3-((4-methylphenyl)aminocarbonylmethyl) indolin-2-one (308 mg) was dissolved in ethanol (15 mL), concentrated sulfuric acid (10 mg) was added, and the mixture was stirred at 15-30° C. for one hour. Water was added to the reaction solution, extraction was performed with ethyl acetate, the organic layer was dried with anhydrous sodium hydrogensulfate and the solvent was distilled off. The reaction mixture was purified by silica gel column chromatography to obtain 225 mg of the title compound (yield: 88%).

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US06716628B2uspto-grants-2004_04