L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]- → (2S)-2-(((tert-butoxy)carbonyl)amino)-3-cyclohexylpropanoic acid

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Reaction Steps

A solution of 30.0 g (0.11 mole) of t-butoxycarbonylphenylalanine in 750 ml of tetrahydrofuran was hydrogenated at 60° for 24 hours using 50 psi hydrogen gas and 5% rhodium on carbon. The mixture was filtered and the filtrate concentrated to give the title compound (30.7 g) as a colorless oil. The oil was used without further purification. Structure assignment was supported by the nmr spectrum (loss of aromatic protons and appearance of cyclohexyl protons).

Provenance & Evidence