Trifluoroacetic acid → HCID 131721464, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (4S,5R,6R)-5-acetylamino-6-(dipropylcarbamoyl)-4-(2,2,2-trifluoroacetylmethylamino)-5,6-dihydro-4H-pyran-2-carboxylic acid, benzhydryl ester (0.430 g) in dichloromethane (2.5 ml) and trifluoroacetic acid (2.5 ml) was stirred at 23° C. for 2 hours. The solvent was removed in vacuo and the residue was azeotroped with toluene (2×25 ml). The residue was taken up in a water/methanol mixture (20 ml, 1:1 v/v) and stirred at 23° C. with potassium carbonate (1.0 g) for 18 hours. The solvent was removed in vacuo and the residue was purified using HPLC on a reverse phase column eluted in a gradient procedure with water and acetonitrile containing trifluoroacetic acid. The required fractions were combined and solvent was removed in vacuo to give the title compound as a white solid (0.182 g). 1H NMR (250 MHz, D6 -DMSO,) 9.00 (2H, broad s), 8.35 (1H, d, J=8 Hz), 5.92 (1H, d, J=3 Hz), 5.05 (1H, d, J=8 Hz), 4.34 (1H, m), 3.46-3.30 (2H, m), 3.25-3.10 (1H, m), 3.08-2.90 (1H, m), 2.6 (3H, s), 1.75 (3H, s), 1.60-1.48 (2H, m), 1.48-1.30 (2H, m), 0.80 (3H, t, J=8 Hz), 0.75 (3H, t, J=8 Hz). Mass spec (Low Resolution): MH+ =342. Mass spec (High Resolution): MH+ =342.202998, fits for molecular formula C16H28N3O5, error=0.3 ppm.

Provenance & Evidence