Triethylamine → HCID 492423, compound

Participants

Reaction Steps

To a stirred solution of (4R,5R,6R)-5-acetylamino-4-azido-6-(dipropylcarbamoyl)-5,6-dihydro-4H-pyran-2-carboxylic acid, methyl ester (500 mg) in tetrahydrofuran (6 ml) under nitrogen was added triphenylphosphine (428 mg). After 3.5 hours at 23° C. water (1 ml) was added adn the solution was stirred for a further 21 hours. Triethylamine (1 ml) was added and stirring was continued for a further 7 hours after which the solvents were removed in vacuo. The resulting liquid was redissolved in ethyl acetate, was dried over anhydrous magnesium sulphate, and the solvent was evaporated in vacuo to leave a yellow solid. The solid was chromatographed over silica (Merck 9385, 45 g) using medium pressure (ca 4 psi) and chloroform/methanol (15:1, v/v) as eluant. Appropriate fractions were combined and the solvent was evaporated in vacuo to afford a white solid which was suspended in water (5 ml) containing triethylamine (2 ml) and was stirred at 50° C. for 1.5 hours. The solvents were removed in vacuo to afford the title compound as a white solid (171 mg). 1H NMR (250MHz, D6 -DMSO) 8.4 (1H, broad s), 5.7 (1H, d, J=1.5Hz), 5.1 (1H, d, J=4Hz), 4.4 (1H, broad s), 3.95 (1H, broad s), 2.95-3.86 (6H, m), 2.0 (3H, s), 1.6 (4H, m), 0.94+0.99 (6H, two t, J=7.5Hz). Mass spec. (low resolution): MH+ =328. Mass analysis: C15H25N3O5. 1.5 H2O Required: C, 50.79; H, 7.90; N, 11.85. Found: C, 50.87; H, 8.04; N, 11.54.

Provenance & Evidence