Triphenylphosphine → HCID 57663206, compound

Participants

Reaction Steps

DIAD (1.18 mL, 6.0 mmol) was added to a stirred solution of methyl 3-hydroxy-5-[(4-methyl-5-oxo-2,3,4,5-tetrahydro-1,4-benzoxazepin-8-yl)oxy]benzoate (1.72 g, 5.0 mmol) and triphenylphosphine (2.62 g, 10.0 mmol) in THF (50 mL) at 0° C.-5° C. The mixture was stirred for 30 minutes, then treated with (R)-1-methoxy-2-propanol (675 mg, 7.5 mmol) and the mixture stirred at RT for 18 hours. The mixture was evaporated in vacuo to a residue which was chromatographed on silica, eluting with 50% ethyl acetate in isohexane. The residue was slurried in ether (25 mL), filtered, and the filtrates evaporated in vacuo to give the desired compound (2.41 g) with a small amount of contaminating triphenylphosphine present. The material was used in the next steps without further purification. 1H NMR δ (CDCl3): 1.25 (d, 3H), 3.15 (s, 3H), 3.3 (s, 3H), 3.4-3.5 (m, 2H), 3.5 (t, 2H), 3.8 (s, 3H), 4.3 (t, 2H), 4.5 (m, 1H), 6.5 (d, 1H), 6.7 (d, 1H), 6.75 (d, 1H), 7.2 (d, 1H), 7.35 (d, 1H), 7.8 (d, 1H); m/z 416 (M+H)+

Provenance & Evidence