Water → HCID 86710247, compound

Participants

Reaction Steps

To a solution of (2R)-4-[4-(1,3-benzoxazol-2-yl)-1H-pyrazol-1-yl]-2-methyl-2-(methylsulfonyl)butanoic acid (0.420 g, 1.16 mmol) in 2-MeTHF (30 mL) was added N-methyl morpholine (0.165 g, 1.62 mmol, 1.4 eq), followed by CDMT (0.244 g, 1.39 mmol, 1.2 eq). The reaction mixture was allowed to stir for one hour. O-tetrahydro-2H-pyran-2-yl-hydroxylamine (0.162 g, 1.39 mmol, 1.2 eq) was added, and the reaction was allowed to stir for an additional two hours. Water (20 mL) was added, and the solution was extracted with 2-MeTHF (100 mL). The aqueous layer was re-extracted with 2-MeTHF (150 mL) and the combined organic layers were washed with brine. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The crude material was purified by flash chromatography, eluting with 30%-100% ethyl acetate/heptane to yield (2R)-4-[4-(1,3-benzoxazol-2-yl)-1H-pyrazol-1-yl]-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (410 mg, 77% yield) as a colorless oil. LC-MS M−H 461.3.

Provenance & Evidence