Hydrochloric Acid → L-Leucine

Participants

Reaction Steps

Synthesis of (S)-(E)-3-(4-morpholine-carbonylleucyl)amino-5-phenyl-1-phenylsulfonyl-1-pentene, abbreviated Mu-Leu-HphVSPh, was as follows. Preparation of Mu-Leu-Hph was achieved by coupling of HCl.HphVSPh (described in the preparation of Mu-Phe-HphVSPh) with leucine morpholine urea (Mu-LeuOH). Mu-LeuOH was prepared in two steps, namely by treating the leucine benzyl ester p-toluenesulfonate (Bachem) with 4-morpholine chloride (Aldrich) in the presence of triethylamine (Aldrich) to give Mu-LeuOBzl in 99% yield. Hydrogenolysis over 5% palladium/charcoal in ethyl acetate afforded the desired product in quantitative yield.

Provenance & Evidence