反应 #215521

反应方程式

4-[N-carbobenzyloxy-(2-cyclohexylethylamino)]phenylacetyl chloride

malic acid

hydrogen

triethylamine

→

O-[4-(2-cyclohexylethylamino)phenylacetyl]malic acid

溶剂

tetrahydrofuran

ether

反应条件

后处理

1. 1
   温度An immediate precipitate forms, but the mixture is refluxed for one hour
2. 2
   过滤filtered while hot
3. 3
   洗涤The solid is washed several times with hot ether
4. 4
   其他the ether is evaporated
5. 5
   其他to yield a white solid
6. 6
   过滤The catalyst is filtered
7. 7
   其他the solution is evaporated
8. 8
   其他The residue is crystallized from acetic acid

实验过程

A warm solution of 4-[N-carbobenzyloxy-(2-cyclohexylethylamino)]phenylacetyl chloride and 1.3 g. triethylamine in 100 ml. ether is treated with 2 g. malic acid. An immediate precipitate forms, but the mixture is refluxed for one hour and filtered while hot. The solid is washed several times with hot ether, then the ether is evaporated to yield a white solid. The product is dissolved in tetrahydrofuran (100 ml.) and hydrogenated over 600 mg. 10% palladium-on-carbon at 50 psi until hydrogen uptake stops. The catalyst is filtered, and the solution is evaporated. The residue is crystallized from acetic acid to yield O-[4-(2-cyclohexylethylamino)phenylacetyl]malic acid.

来源