Hydrochloric Acid → HCID 86599483, compound

Participants

Reaction Steps

The 7-{4-[(tert-butoxycarbonyl)amino]benzyl}-6-chloro-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid (300 mg, 0.62 mmole) was stirred in 3 mL dioxane and 0.62 mL HCl (4M) in dioxane for 6 hrs. 1HNMR indicated that the reaction mixture was 1:1 ratio of starting material:product. Additional 0.3 mL 12 N HCl in 2 mL water was added to above mixture. After the mixture was stirred for overnight, 0.3 mL 12 N HCl was added. After another overnight stirring, the solution of 3 mL 12 N HCl in 3 mL MeOH and 3 mL water was added to above mixture and the mixture was stirred for 6 hrs. The mixture was purified by RPHPLC elute with 20 to 65% ACN in water with 0.1% TFA to give the desired product as a white solid with >95% purity: ESHRMS m/z 384.0594 (M+H, C18H14O3F3ClN, Calc'd 384.0609). 1H NMR (acetone-d6/400 MHz) 7.87 (s, 1H), 7.58(s, 1H), 7.39 (d, 1H, J=8.4 Hz), 7.22 (d, 1H, J=8.4 Hz), 6.02 (s, 1H), 5.82 (q, 1H, J=7.2 Hz), 4.15 (m, 2H).

Provenance & Evidence