tert-Butyl isothiocyanate → ethyl (2R)-5-{[(benzyloxy)carbonyl]amino}-2-(3-tert-butylthioureido)pentanoate

Participants

Reaction Conditions

Reaction Steps

7.5 cm3 of tert-butyl isothiocyanate are added to a solution of 13 g of ethyl (2R)-2-amino-5-[(benzyloxy)carbonyl]amino-pentanoate hydrochloride in 200 cm3 of ethanol, and the mixture is then stirred at a temperature in the region of 20° C. After 48 hours, the reaction medium is concentrated under reduced pressure (1 kPa) at a temperature in the region of 40° C. to give 16 g of ethyl (2R)-5-{[(benzyloxy)carbonyl]amino}-2-(3-tert-butyl-thioureido)pentanoate in the form of a colorless oil [mass spectrum: EI m/z=409 M+ m/z=232 (C13H14NO3)+ m/z=142 (232-PhCH)+ m/z=91 (C7H7)+].

Provenance & Evidence