Hydrogen Peroxide → HCID 131713561, compound

Participants

Reaction Steps

A solution of N-methyl-L-tyrosyl-N-(3-phenylpropyl)-D-methioninamide monohydrochloride hydrate (4:1) (690 mg.) and aqueous hydrogen peroxide (3%, 1.95 ml.) in acetic acid (10 ml.) was stirred at room temperature, then stripped of volatiles. The residue was purified by reverse phase high pressure liquid chromatography on octadecylsilated silica gel (350 g.) using ammonium acetate (0.2%) in methanol-water (1:1) as the eluant. A solution of the product, which appeared in fractions 4-5 (centered at k'=2.0), in methanol (20 ml.) and hydrochloric acid (0.01 N, 100 ml.) was concentrated (to 60 ml.), filtered and lyophilized, affording as an amorphous solid N-methyl-L-tyrosyl-N-(3-phenylpropyl)-D-methioninamide S-oxide monohydrochloride hemihydrate (558 mg.; [α]D25 +59.8°, c=1, methanol), whose free base is the compound of Formula II wherein Q is Met(O), R1 is methyl, R2 and R5 are each hydrogen and R4 is (CH2)nY wherein n is 3 and Y is phenyl.

Provenance & Evidence