Lithium Hydroxide → HCID 71679190, compound

Participants

Reaction Steps

Followed general procedure using: the corresponding peptidomimetic epoxide ethyl ester 17e (76.4 mg, 0.16 mmol); LiOH (8 mg, 0.34 mmol); after extraction afforded the desired product as a white solid (51 mg, 71.5%). 1H NMR (DMSO-d6, 400 MHz): δ 12.52 (s, 1H); 8.78-8.76 (d, 1H, J=8.0 Hz); 7.94-7.92 (t, 2H); 7.63 (s, 1H); 7.29-7.24 (t, 2H); 4.58-4.57 (m, 1H); 3.62-3.61 (d, 1H, J=1.80 Hz); 3.41-3.40 (d, 1H, J=1.80 Hz); 1.64-1.51 (m, 3H): 0.91-0.88 (dd, 6H). 13C NMR (DMSO-d6, 100 MHz): 171.02, 166.26, 162.88, 160.46, 157.72, 147.81, 130.80, 130.77, 127.62, 127.54, 115.59 (d, J=21.6 Hz); 107.97, 52.36, 52.08, 51.37, 28.89, 24.25, 22.82, 21.19. EST-HRMS (m/z): [M+H+] calcd for C19H20FN3O5S: 422.1180, observed: 422.1186. HPLC Method 1: Rt=23.8 min, purity=95.1%.

Provenance & Evidence