反応 #215521

反応方程式

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

malic acid

hydrogen

triethylamine

→

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

溶媒

tetrahydrofuran

ether

反応条件

後処理

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

実験手順

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.

出典