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

Participants

Reaction Steps

Proceeding as in Example 1, but substituting 2-(2H-1,2,3-triazol-2-yl)acetic acid hydrochloride and (2S,4R)-4-(2-chlorobenzyl)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 56, (2S,4R)-1-(2-(2H-1,2,3-triazol-2-yl)acetyl)-4-(2-chlorobenzyl)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide (70 mg, 55%). Major isomer: 1H-NMR (400 MHz, DMSO-D6): σ 10.00 (s, 1H), 7.80 (s, 2H), 7.58-7.51 (m, 2H), 7.48-7.39 (m, 2H), 7.35-7.25 (m, 2H), 7.23-7.15 (m, 2H), 7.06-6.91, (m, 4H), 5.50 (q, 2H), 4.56-4.48 (m, 1H), 3.92-3.81 (m, 1H), 3.44-3.36 (m, 1H), 2.94-2.73 (m, 3H), 2.28-1.86 (m, 2H). MS (EI) for C28H25ClFN5O3. found 533.9 (MH+).

Provenance & Evidence