(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide → (S)-3-(benzyloxy)-2-(2-(3,5-dimethyl-1H-pyrazol-4-yl)acetamido)-N-(4-(4-fluorophenoxy)phenyl)propanamide

Participants

Reaction Steps

Proceeding as in Example 1, but substituting 2-(3,5-dimethyl-1H-pyrazol-4-yl)acetic acid hydrochloride and (S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide, gave Compound 152, (S)-3-(benzyloxy)-2-(2-(3,5-dimethyl-1H-pyrazol-4-yl)acetamido)-N-(4-(4-fluorophenoxy)phenyl)propanamide (28 mg, 42%); Major isomer: 1H-NMR (400 MHz, DMSO-D6): σ 11.96 (br s, 1H) 10.20 (br s, 1H), 8.12-8.10 (d, 1H), 7.63-7.59 (d, 2H), 7.33-7.27 (m, 5H), 7.23-7.19 (t, 2H), 7.04-6.96 (m, 4H), 4.71-4.66 (m, 1H), 4.51 (s, 2H), 3.68-3.61 (d, 2H), 3.22 (s, 2H), 2.07 (s, 6H). MS (EI) for C29H29FN4O4. found 517.0 (MH+).

Provenance & Evidence