Trifluoroacetic acid → 3-{2-Cyclohexylcarbamoyloxymethyl-4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]phenyl}propionic acid

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Reaction Steps

A 25 mL round bottomed flask was charged with 3-{2-cyclohexylcarbamoyloxymethyl-4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]phenyl}-propionic acid tert-butyl ester (0.080 g, 0.14 mmol) and CH2Cl2 (2 mL). Trifluoroacetic acid (2 mL) was added, and the solution was stirred at ambient temperature under a nitrogen atmosphere for 1.5 h. The solution was concentrated to give a white solid (0.068 g, 94%). 1H NMR (400 MHz, CDCl3) 1.08-1.18 (m 3H), 1.21-1.42 (m, 2H), 1.57 (br s, 1H), 1.66-1.70 (m, 2H), 1.90 (br s, 2H), 2.40 (s, 3H), 2.61 (t, J=7.7 Hz, 2H), 2.94 (t, J=7.8 Hz, 2H), 3.01 (t, J=6.4 Hz, 2H), 3.48 (br s, 1H), 4.22 (t, J=6.4 Hz, 2H), 4.74 (br s, 1H), 5.07 (s, 2H), 6.79-6.89 (m, 1H), 6.90 (s, 1H), 7.11 (d, J=8.3 Hz, 1H), 7.44-7.46 (m, 3H), 7.98 (dd, J=6.7, 2.8 Hz, 2H). MS (ES) m/e 507 (M+1).

Provenance & Evidence