Acetic Acid → HCID 70510747, compound

Participants

Reaction Steps

A mixture of (N-benzyloxycarbonyl-O-benzyl-L-tyrosyl)-N-(3-phenylpropyl)-D-serinamide (1.25 g.), acetic acid (125 mg.) and palladium on carbon (10%, 100 mg.) in methanol (50 ml.) was hydrogenated under pressure for 30 hours, then filtered. The filtrate was 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, and an aqueous solution of the product was lyophilized, affording as an amorphous white solid L-tyrosyl-N-(3-phenylpropyl)-D-serinamide hydrate (3:2) (245 mg.; [α]D25 +16.9°, c=1, methanol), whose unsolvated form is the compound of Formula II wherein Q is Ser, R1, R2 and R5 are each hydrogen and R4 is (CH2)nY wherein n is 3 and Y is phenyl.

Provenance & Evidence