Lithium Hydroxide → HCID 71679024, compound

Participants

Reaction Steps

Synthesized following general saponification procedure using the following quantities: the corresponding peptidomimetic epoxide ethyl ester 21 (93 mg, 0.19 mmol); LiOH (4.5 mg, 0.19 mmol); THF/MeOH/H2O (1.5 mL: 0.5 mL: 0.5 mL); yielded 36 as a white solid (29 mg, 33.1%). 1H NMR (400 MHz, DMSO-d6): 12.50 (bs, 1H), 8.82-8.80 (d, 1H): 7.93-7.91 (m, 2H); 7.76 (s, 1H); 7.63 (s, 1H); 7.46-7.24 (t, 2H); 6.99 (s, 1H); 4.79-4.74 (m, 1H); 3.67-3.66 (d, 1H); 3.62 (s, 3H); 3.49-3.48 (d, 1H); 3.12-2.90 (m, 2H). 13C NMR (400 MHz, DMSO-d6): 169.72, 168.60, 165.56, 162.97, 160.54, 157.78, 147.88, 137.17, 130.84, 127.71, 127.63, 118.35, 115.68, 115.47, 108.08, 53.07, 52.98, 51.56, 33.11, 29.60. ESI-HRMS (m/z): [M+H+] calcd. for C20H18FNO5S: 460.1085, observed: 460.1090. Rt=18.1 min, purity=95.3%.

Provenance & Evidence