Acetic Acid → HCID 68679787, compound

Participants

Reaction Conditions

Reaction Steps

Add a solution of 2-[tert-Butoxycarbonyl-(3-methoxycarbonyl-propyl)-amino]-5-methyl-4-trifluoromethoxy-benzoic acid methyl ester (1.1 g, 2.4 mmol), in toluene (25 mL) to a solution of potassium t-butoxide (0.51 g, 4.9 mmol) in toluene (75 mL) at 100° C. over 30 min. After heating for 1 h cool the reaction to room temperature and quench the reaction with acetic acid (5.0 mmol). Dilute the reaction with ethyl acetate (100 mL) and wash with water (2×200 mL) followed by brine (200 mL). Dry the organics over sodium sulfate and remove solvent under vacuum. Dissolve the residue in acetic acid (25 mL) and dilute with concentrated HCl (15 mL) and water (10 mL). Heat the mixture at 100° C. for 2 h then cool to room temperature. While cooling in an ice bath neutralize the reaction with 5 N NaOH. Extract the organics with ethyl acetate (200 mL) and wash the organic with brine (100 mL). Remove solvent under vacuum and chromatograph the crude product over silica gel using ethyl acetate/hexane (5-20%) to elute. This provides the title compound (0.28 g, 44%) as an oil that crystallizes upon standing: H NMR (CDCl3, 400 MHz) δ 2.11-2.18 (m, 5H), 2.81 (t, J=6.8 Hz, 2H), 3.24 (t, J=6.8 Hz, 2H), 6.61 (m, 1H), 7.59 (s, 1H). MS (ES+): 260 (M+H).

Provenance & Evidence