Triethylamine → HCID 178519140, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of trans-4-(4-(trifluoromethyl)phenylsulfonamido)cyclohexanecarboxylic acid (Intermediate 18, 110 mg, 0.313 mmol,), (S)-4-phenyloxazolidin-2-one (25.5 mg, 0.157 mmol) in toluene (2 ml) was added triethylamine (0.087 ml, 0.626 mmol). The mixture was heated to 80° C. to obtain a solution. Pivaloyl chloride (0.039 ml, 0.313 mmol) in toluene (1 ml) was added to the reaction mixture, and it was heated to 110° C. with stirring for 18 hr. The reaction mixture was then diluted with 1M HCl and extracted with DCM. The DCM layer was dried (MgSO4), then filtered and concentrated in vacuo to a tanned solid. The crude material was purified via normal phase chromatography on biotage SP1, using 25+M column and a calculated gradient from 50% EtOAc in heptane, to yield the title compound as a white solid (8 mg, 10%). MS MH+ 497.2

Provenance & Evidence