Hydrogen Peroxide → HCID 86739482, compound

Participants

Reaction Steps

A solution of L-tyrosyl-N-methyl-N-(3-phenylpropyl)-D-methioninamide monohydrochloride (1.3 g.) and aqueous hydrogen peroxide (3%, 2.7 ml.) in acetic acid (10 ml.) was stirred at room temperature for two hours, the concentrated. The residue was evaporated twice from ethyl acetate then purified by reverse phase high pressure liquid chromatography on octadecylsilated silica gel (350 g.) using ammonium acetate (0.15%) in methanol-water (3:2) as the eluant (200 ml./min.). A solution of the product (1.0 g.), which appeared in fraction 2 (k'=1.4-3.0), in hydrochloric acid (0.0936N, 30 ml.) and water (30 ml.) was lyophilized, affording L-tyrosyl-N-methyl-N-(3-phenylpropyl)-D-methioninamide S-oxide monohydrochloride monohydrate ([α]D25 +61.4°, c=1, methanol), whose free base is the compound of Formula II wherein Q is Met(O), R1 and R2 are each hydrogen, R4 is (CH2)nY wherein n is 3 and Y is phenyl and R5 is methyl.

Provenance & Evidence