Hydrochloric Acid → HCID 58005171, compound

Participants

Reaction Steps

(2S)-[(tert-butoxycarbonyl)amino](cyclohexyl)acetic acid (1.05 eq.), DIPEA (3.2 eq.) and TBTU (1.1 eq.) were added to a 0.12M solution of methyl (4R)-4-[(3′-bromobiphenyl-3-yl)methoxy]-L-prolinate hydrochloride 97 in DMF. The reaction mixture was stirred at RT for 2 h then it was diluted with EtOAc:H2O and acidified with aqueous (1N) HCl. The phases were separated and the organic layer was washed sequentially with aqueous (1N) HCl, aqueous (2N) NaOH and brine, dried (Na2SO4) and evaporated under reduced pressure to afford the title compound 106 (95% crude yield) as a pale yellow foam which was used without further purification. 1H NMR (400 MHz, DMSO-d6, 300 K) δ 7.86 (s, 1H), 7.70 (d, J 7.8, 1H), 7.66-7.57 (m, 3H), 7.54-7.33 (m, 3H), 6.94 (d, J 8.6, 1H), 4.65 (d, J 11.6, 1H), 4.58 (d, J 11.6, 1H), 4.36 (t, J 8.5, 1H), 4.32 (bs, 1H), 4.19 (d, J 11.1, 1H), 4.11 (t, J 11.1, 1H), 3.74-3.66 (m, 1H), 3.65 (s, 3H), 2.48-2.35 (m, 1H), 2.08-1.97 (m, 1H), 1.83-1.55 (m, 6H), 1.44-1.37 (m, 1H), 1.34 (s, 9H), 1.22-1.09 (m, 2H), 1.08-0.93 (m, 2H). MS (ES+) m/z 629, 631 (M+H)+

Provenance & Evidence