2-[3(S)-(tert-butoxycarbonyl)amino-5(S)-(p-tert-butyl-benzyl)-2(S)-hydroxy-6-methyl-heptyl]-N-butyl-acrylamide → 5(S)-(tert-butoxycarbonyl)amino7(S)-(p-tert-butyl-benzyl)-4(S)-hydroxy-2(R,S),8-dimethyl-nonanoic acid N-(butyl)amide

Participants

Reaction Steps

150 mg of 2-[3(S)-(tert-butoxycarbonyl)amino-5(S)-(p-tert-butyl-benzyl)-2(S)-hydroxy-6-methyl-heptyl]-N-butyl-acrylamide (diastereoisomer I, Application Example 2b) are hydrogenated in the presence of 150 mg of 10% Pd/C in tetrahydrofuran (20 ml) for 2 hours at room temperature and under normal pressure. The reaction mixture is filtered and concentrated by evaporation. The residue is purified by FC (50 g of silica gel, dichloro-methane/diethyl ether 8:2). The title compound is obtained in the form of a diastereoisomeric mixture: Rf (dichloromethane/diethyl ether 8:2)=0.18.

Provenance & Evidence