2-(1H-1,2,4-triazol-1-yl)acetic acid hydrochloride → (2S,4R)-1-(2-(1H-1,2,4-triazol-1-yl)acetyl)-4-(3-fluorobenzyl)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide

Participants

Reaction Steps

Proceeding as in Example 1, but substituting 2-(1H-1,2,4-triazol-1-yl)acetic acid hydrochloride and (2S,4R)-4-(3-fluorobenzyl)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 51, (2S,4R)-1-(2-(1H-1,2,4-triazol-1-yl)acetyl)-4-(3-fluorobenzyl)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide (59 mg, 31%). Major isomer: 1H-NMR (400 MHz, DMSO-D6): σ 10.00 (s, 1H), 8.42 (s, 1H), 7.95 (s, 1H), 7.58-7.52 (m, 2H), 7.40-7.31 (m, 1H), 7.25-6.92 (m, 10H), 5.24 (q, 2H), 4.55-4.48 (m, 1H), 3.89-3.76 (m, 1H), 2.84-2.66 (m, 3H), 2.03-1.90 (m, 2H). MS (EI) for C28H25F2N5O3. found 517.9 (MH+).

Provenance & Evidence