Hydrochloric Acid → methyl 3-(S)-((3,5-bis(trifluoromethyl)phenyl)carbonylamino)-2-(R)-(4-fluorophenyl)cyclopentane-1-(R)-carboxylate

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Reaction Steps

To a solution of 100 mg of amine from Example 62 in 5 mL of methylene chloride was added 0.2 mL of DIPEA and 175 mg of 3,5-bis(trifluoromethyl)benzoyl chloride. The reaction was stirred at room temperature for 1 h and was then poured into water and 2N HCl and extracted twice with methylene chloride. The organic layers were washed with a portion of brine, combined, dried over sodium sulfate and evaporated. The residue was purified by flash chromatography eluting with 30 to 50% ethyl acetate in hexanes to obtain 100 mg of title compound. NMR (CDCl3): δ 1.8-1.9 (m, 1H), 2.05-2.2 (m, 1H), 2.2-2.4 (m, 2H), 3.08 (q, 1H), 3.42 (t, 1H), 3.67 (s, 3H), 4.65 (p, 1H), 6.80 (d, 1H), 6.99 (t, 2H), 7.22 (dd, 2H), 7.96 (s, 1H), 8.15 (s, 2H).

Provenance & Evidence