Water → HCID 492429, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (4S,5R,6R)-4-azido-6-(dipropylcarbamoyl)-5-(2,2,2-trifluoroacetylamino)-5,6-dihydro-4H-pyran-2-carboxylic acid, methyl ester (1 g) in dry tetrahydrofuran (10 ml) was added triphenylphosphine (0.75 g) and the reaction was stirred under nitrogen at 23° C. for 1.5 hours. To this was added water (2 ml) and triethylamine (2 ml) and the mixture was stirred for 16 hours at 23° C. The solvent was removed in vacuo and the residue was chromatographed over silica (Merck 9385, 50 g) using medium pressure (ca 4 psi) and dichloromethane/methanol (15:1 v/v) as the eluant. The required fractions were combined and the solvent removed in vacuo to give the title compound as a white solid. (0.87 g). 1H NMR (250 MHz, D6 -DMSO) 9.25 (1H, d, J=9 Hz), 5.90 (1H, d, J=3 Hz), 4.79 (1H, d, J=9 Hz), 4.00 (1H, m), 3.71 (3H, s), 3.58 (1H, m), 3.40 (2H, m), 3.16 (1H, m), 2.95 (1H, m), 1.84 (2H, s), 1.57 (2H, m), 1.40 (2H, m), 0.81 (6H, m), Mass analysis: C16H24F3N3O5. 0.5 H2O. Required: C, 47.52; H, 6.23; N, 10.39. Found: C, 47.68; H, 6.05; N, 10.10.

Provenance & Evidence