Diisopropylethylamine → (R)-3-benzoylamino-3-(4-{3-methoxy-4-[3-(2-methylphenyl)ureido]-phenylacetyl-amino}-phenyl)-propanoic acid methyl ester

Participants

Reaction Steps

A solution of 3-methoxy-4-[3-(2-methylphenyl)ureido]phenylacetic acid (1.52 g, prepared as described in Reference Example 31) in anhydrous dimethylformamide (40 ml), under an atmosphere of argon, was treated sequentially with O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (1.84 g), diisopropylethylamine (3.4 ml) and a solution of (R)-3-benzoylamino-3-(4-aminophenyl)-propanoic acid methyl ester [2.0 g, Reference Example 13(a)] in dimethylformamide (10 ml). After stirring for 45 minutes at ambient temperature the reaction mixture was evaporated. The residue was treated with water (150 ml) and hydrochloric acid (10 ml, 1M) was added to the aqueous slurry. The mixture was filtered and the insoluble material was washed three times with water (50 ml) then dried in vacuo to give the title compound as white solid (2.53 g).

Provenance & Evidence