Sodium Bicarbonate → Trifluoroacetic acid

Participants

Reaction Steps

(S)-3-[(S)-2-Amino-1-(4-trifluoromethylphenoxy)ethyl]pyrrolidine-1-carboxylic acid t-butyl ester (35.0 mg, 0.093.5 mol, 1.0 eq.) was dissolved in DCM (1.2 mL) and triethylamine (39.1 μL). A solution of 4-(1,3-oxazol-5-yl)benzenesulfonyl chloride (56.9 mg, 234 μmol, 2.5 eq.) in DCM (0.4 mL,) was then added. The resulting mixture was stirred for 1 hour at room temperature. Saturated sodium bicarbonate was then added (1 mL) and the mixture was diluted with DCM (2 mL). The organic layer was collected and concentrated under reduced pressure. The crude material was redissolved in 1.2 M of HCl in EtOH (1.9 mL) and stirred at room temperature overnight. The mixture was then concentrated under reduced pressure then redissolved in 1:1 AcOH/H2O (1.5 mL) and purified by preparative HPLC to yield the title compound as a TFA salt (20.1 mg). MS m/z: [M+H]+ calcd for C22H22F3N3O4S, 482.13. found 482.4.

Provenance & Evidence