benzyl (3R,5S)-5-(4-(4-fluorophenoxy)phenylcarbamoyl)pyrrolidin-3-ylcarbamate → benzyl (3R,5S)-1-(2-(1H-imidazol-5-yl)acetyl)-5-(4-(4-fluorophenoxy)phenylcarbamoyl)pyrrolidin-3-ylcarbamate

Participants

Reaction Steps

Proceeding as in Example 1, but substituting 4-imidazoleacetic acid hydrochloride and benzyl (3R,5S)-5-(4-(4-fluorophenoxy)phenylcarbamoyl)pyrrolidin-3-ylcarbamate gave Compound 253, benzyl (3R,5S)-1-(2-(1H-imidazol-5-yl)acetyl)-5-(4-(4-fluorophenoxy)phenylcarbamoyl)pyrrolidin-3-ylcarbamate (1.01 g, 1.80 mmol, 67% yield). 1H-NMR (400 MHz, DMSO-d6): 11.92 (s, 1H), 10.06 (s, 1H), 7.92-7.42 (m, 4H), 7.40-7.28 (m, 5H), 7.23-7.17 (m, 2H), 7.06-6.94 (m, 5H), 5.02 (s, 2H), 4.50 (m, 1H), 4.28-4.13 (m, 1H), 3.85-3.41 (m, 4H), 2.38-2.02 (m, 2H). MS (EI) for C30H28FN5O5. found 557.9 (MH+).

Provenance & Evidence