Trifluoroacetic acid → 6-(5-((S)-2-amino-3-(4(trifluoromethyl)phenyl)propylamino)-1,3,4-thiadiazol-2-yl)benzo[d]oxazol-2(3H)-one

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Reaction Steps

tert-Butyl (S)-1-(5-(2-oxo-2,3-dihydrobenzo[d]oxazol-6-yl)-1,3,4-thiadiazol-2-yl-boc-amino)-3-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate (130 mg, 205 μmol) in 10 mL DCM was treated with 10 mL TFA for 60 minutes. After removing the solvent, the remaining residue was dissolved in 100 mL EtOAc. The resulting solution was washed with a mixture of aqueous saturated sodium bicarbonate plus 5% 5N NaOH, then twice with saturated sodium bicarbonate. The organic layer was dried over sodium sulfate. Removal of the solvent gave the title compound 6-(5-((S)-2-amino-3-(4(trifluoromethyl)phenyl)propylamino)-1,3,4-thiadiazol-2-yl)benzo[d]oxazol-2(3H)-one as an off-white amorphous solid (47 mgs, 53%). LCMS (API-ES) m/z (%): 436.0 (100%, M++H); 1H NMR (400 MHz, CD3OD) δ ppm 2.78 (dd, J=13.60, 7.53 Hz, 1H) 2.99 (dd, J=13.60, 5.58 Hz, 1H) 3.35-3.40 (m, 1H) 3.40-3.47 (m, 1H) 3.48-3.55 (m, 1H) 7.13 (d, J=8.22 Hz, 1H) 7.48 (d, J=8.02 Hz, 2H) 7.53 (dd, J=8.12, 1.47 Hz, 1H) 7.62 (d, J=7.24 Hz, 3H).

Provenance & Evidence