Triphenylphosphine → N-[(4R,4aR,6R,8aS)-6-cyclopropyl-8a-(2,4-difluorophenyl)-4-methyl-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide

Participants

Reaction Steps

Diethyl azodicarboxylate (92 μL, 0.59 mmol) was added to a 0° C. solution of triphenylphosphine (153 mg, 0.583 mmol) in tetrahydrofuran (7 mL), and the mixture was stirred for 10 minutes in the ice bath. A solution of N-({(3S,4R,6R)-6-cyclopropyl-3-(2,4-difluorophenyl)-4-[(1S)-1-hydroxyethyl]tetrahydro-2H-pyran-3-yl}carbamothioyl)benzamide (C30) (90 mg, 0.20 mmol) in tetrahydrofuran (2 mL) was added drop-wise to the reaction mixture, which was then stirred for 1 hour under ice cooling. The reaction mixture was concentrated in vacuo; purification via silica gel chromatography (Gradient: 0% to 80% ethyl acetate in heptane) afforded the product as a gum. Yield: 45 mg, 0.10 mmol, 50%. LCMS m/z 441.1 [M−H+].

Provenance & Evidence