[1-Benzyl-3-(benzyloxycarbonyl-isobutyl-amino)-2-hydroxy-propyl]-carbamic Acid hexahydro-furo[2,3-b]furan-3-yl Ester → (1-Benzyl-2-hydroxy-3-isobutylamino-propyl)-carbamic acid hexahydro-furo[2,3-b]furan-3-yl ester

Participants

Reaction Steps

A mixture of [3-(hexahydro-furo[2,3-b]furan-3-yloxycarbonylamino)-2-hydroxy-4-phenyl-butyl]-isobutyl-carbamic acid benzyl ester 18 (5.5 g, 10.4 mmol) and 550 mg of 10% Pd/C in 130 ml of ethanol was stirred under a hydrogen atmosphere overnight. The catalyst was removed by filtration through Celite®, and the solution was evaporated to dryness to yield (1-benzyl-2-hydroxy-3-isobutylamino-propyl)-carbamic acid hexahydro-furo[2,3-b]furan-3-yl ester 19 (4.0 g, 97%) as a white solid. TLC: Rf 0.36 (5:15:85 triethylamine:methanol:ethyl acetate). MS 393 (MH)+.

Provenance & Evidence