Trifluoroacetic acid → HCID 24875124, compound

Participants

Reaction Steps

To a solution of [4-[(5-cyano-1H-imidazole-2-carbonyl)-amino]-3-(4,4-dimethyl-cyclohex-1-enyl)-phenyl]-hydroxy-acetic acid ethyl ester (as prepared in the previous step)(30.0 mg, 71 μmol) in 0.2 mL of EtOH at RT was added a 2N KOH solution (71 uL, 14.2 μmol) and the reaction stirred for 2 h. The pH was then adjusted to 2 with a 2 M TFA solution and the title compound was purified by RP-HPLC, eluting with a linear gradient of 20% to 50% CH3CN in 0.1% TFA/H2O over 10 min to give 20 mg (71%) of a white solid. 1H-NMR (400 MHz, CD3OD): δ 8.24 (d, J=8.4 Hz, 1H), 8.00 (s, 1H), 7.40 (dd, J=8.4, 2.1 Hz, 1H), 7.33 (d, J=2.1 Hz, 1H), 5.78 (m, 1H), 5.15 (s, 1H), 2.33 (m, 2H), 2.10 (m, 2H), 1.62 (t, J=6.3, 6.3 Hz, 2H), 1.11 (s, 6H). Mass spectrum (ESI, m/z): Calcd. for C21H22N4O2, 395.2 (M+H). found 395.1.

Provenance & Evidence