Reaktion #82368

Reaktionsgleichung

N2 [3(S)-amino-2(R)-hydroxy-4-phenylbutyl]-N1 -tert.butyl-L-prolinamide

N-(benzyloxycarbonyl)-S-methyl-L-cysteine

hydroxybenzotriazole

N-ethylmorpholine

dicyclohexylcarbodiimide

→

N1 -tert.butyl-L-prolinamide

Lösungsmittel

ethyl acetate

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationfiltered
2. 2
   WaschenThe filtrate was washed with aqueous sodium bicarbonate solution and sodium chloride solution
3. 3
   SonstigeThe solvent was removed by evaporation
4. 4
   Sonstigethe residue was chromatographed on silica gel using System G for the elution

Vorschrift

A solution of 650 mg of N2 -[3(S)-amino-2(R)-hydroxy-4-phenylbutyl]-N1 -tert.butyl-L-prolinamide and 538 mg of N-(benzyloxycarbonyl)-S-methyl-L-cysteine in 20 ml of dry tetrahydrofuran was cooled in an ice/salt mixture. 270 mg of hydroxybenzotriazole, 230 mg of N-ethylmorpholine and 412 mg of dicyclohexylcarbodiimide were added and the mixture was stirred for 16 hours. The mixture was diluted with ethyl acetate and filtered. The filtrate was washed with aqueous sodium bicarbonate solution and sodium chloride solution. The solvent was removed by evaporation and the residue was chromatographed on silica gel using System G for the elution to give 800 mg of N2 -[3(S)-[N-(benzyloxycarbonyl)-S-methyl-L-cysteinyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N1 -tert.butyl-L-prolinamide; MS: m/e 585 [M+H]+.

Quelle