(S)-1-(5-Methyl-1,3,4-oxadiazol-2-yl)-2-phenylethanamine → (S)-2-((S)-3,3-Dimethyl-2-((S)-2-(methylamino)propanamido)butanoyl)-7-((3R,5S)-1-((S)-3,3-dimethyl-2-((S)-2-(methylamino)propanamido)butanoyl)-5-(((S)-1-(5-methyl-1,3,4-oxadiazol-2-yl)-2-phenylethyl)carbamoyl)pyrrolidin-3-yl)-N-((R)-1,2,3,4-tetrahydronaphthalen-1-yl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide

Participants

Reaction Steps

Following procedures analogous to those for the preparation of Compounds F and G of Example 46, (S)-2-((2S,4R)-1-((S)-2-((S)-2-((tert-butoxycarbonyl)(methyl)amino)propanamido)-3,3-dimethylbutanoyl)-4-((S)-2-((S)-2-((S)-2-((tert-butoxycarbonyl)(methyl)amino)propanamido)-3,3-dimethylbutanoyl)-3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-1,2,3,4-tetrahydroisoquinolin-7-yl)pyrrolidine-2-carboxamido)-3-phenylpropanoic acid (Compound D of Example 46, 50 mg, 0.049 mmol) and (S)-1-(5-methyl-1,3,4-oxadiazol-2-yl)-2-phenylethanamine (10 mg, 0.049 mmol) were converted to the title compound (26 mg, 53% over 2 steps). MS (ESI+) m/z 1001.8 (M+H)+.

Provenance & Evidence