(S)-2-((S)-2-((S)-2-((S)-2-((tert-Butoxycarbonyl)(methyl)amino)propanamido)-3,3-dimethylbutanoyl)-7-((3R,5S)-1-((S)-2-((S)-2-((tert-butoxycarbonyl)(methyl)amino)propanamido)-3,3-dimethylbutanoyl)-5-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)pyrrolidin-3-yl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamido)-3-phenylpropanoic acid → (S)-1-(5-Methyl-1,3,4-oxadiazol-2-yl)-2-phenylethanamine

Participants

Reaction Steps

Following a procedure analogous to that for the synthesis of Compound B of Example 78, (S)-tert-butyl (1-(5-methyl-1,3,4-oxadiazol-2-yl)-2-phenylethyl)carbamate (130 mg, 0.43 mmol) was converted to the title compound (45 mg, 52% over 2 steps) after preparative HPLC. 1H NMR (CDCl3) δ 7.38-7.14 (m, 1H), 4.43 (dd, J=8.4, 5.5 Hz, 1H), 3.27 (dd, J=13.6, 5.3 Hz, 1H), 3.04 (dd, J=13.6, 8.4 Hz, 1H), 2.53 (s, 3H); MS (ESI+) m/z 204.2 (M+H)+.

Provenance & Evidence