Reaktion #215521

Reaktionsgleichung

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

malic acid

hydrogen

triethylamine

→

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

Lösungsmittel

tetrahydrofuran

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAn immediate precipitate forms, but the mixture is refluxed for one hour
2. 2
   Filtrationfiltered while hot
3. 3
   WaschenThe solid is washed several times with hot ether
4. 4
   Sonstigethe ether is evaporated
5. 5
   Sonstigeto yield a white solid
6. 6
   FiltrationThe catalyst is filtered
7. 7
   Sonstigethe solution is evaporated
8. 8
   SonstigeThe residue is crystallized from acetic acid

Vorschrift

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.

Quelle