Lithium Hydroxide → HCID 178522495, compound

Participants

Reaction Steps

Synthesized following general saponification procedure using the following quantities: the corresponding peptidomimetic epoxide ethyl ester 18f (125 mg, 0.26 mmol); LiOH (6.2 mg, 0.26 mmol); THF/MeOH/H2O (1.5 mL: 1.0 mL: 0.5 mL); yielded 31b as a white solid (46 mg, 39.1%). 1H NMR (400 MHz, MeOD-d4): δ 11.88 (bs, 1H), 8.89-8.83 (dd, 1H, J=7.4 Hz, J=7.4 Hz); 7.91-7.89 (d, 1H, J=2.5 Hz); 7.78-7.72 (q, 1H); 7.56 (s, 1H); 7.30 (td, 1H, J=2.6 Hz); 6.85 (s, 1H); 4.81-4.76 (m, 1H): 3.76-3.74 (dd, 1H, J=1.68 Hz); 3.45-3.43 (dd, 1H, J=1.65 Hz); 3.11-3.00 (m, 2H). 13C NMR (DMSO-d6, 100 MHz): 171.13, 167.48, 165.83, 160.32, 158.21, 145.64, 135.40, 133.23, 122.17, 114.83, 108.74, 53.86, 53.40, 51.86. ESI-HRMS (m/z): [M+H+] calcd. for C17H14FN5O5S: 420.0773, observed: 420.0769.

Provenance & Evidence