Diisopropylethylamine → HCID 57128419, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (2R,3R,4S)-3-acetylamino-4-(tert-butyldiphenylsilanyloxy)-3,4-dihydro-2H-pyran-2,6-dicarboxylic acid, 6-methyl ester (2.0 g), (2-biphenyl-4-yl-ethyl)propylamine hydrochloride (1.33 g) and diisopropyl ethylamine (2.52 ml) in anhydrous dimethylformamide (5 ml) was added 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyl-uronium tetrafluoroborate (1.55 g). The reaction was stirred at 23° C. for 24 hours then diluted with ethyl acetate (200 ml) and washed with water (2×200 ml), dilute hydrochloric acid (100 ml), saturated sodium bicarbonate solution (100 ml) and brine (100 ml). The organic phase was dried over anhydrous magnesium sulphate and the solvent was removed in vacuo and the residue was chromatographed over silica (Merck 9385, 20 g) using medium pressure (ca 4 psi) and cyclohexane/ethyl acetate (10:1 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 (1.6 g). 1H NMR (250 MHz, D6 -DMSO rotamers) 8.16+8.12 (1H,2×d, J=10 Hz), 7.64 (8H, m), 7.53-7.30 (11H, m), 5.50 (1H, m), 5.11 (1H, m), 4.54+4.40 (1H, 2×m), 4.26 (1H, m), 3.71+3.65 (3H, 2×s), 3.6-3.1 (4H, m), 2.92 (1H, m), 2.82 (1H, m), 1.81+1.79 (3H, 2×s), 1.62 (1H, m), 1.52 (1H, m), 1.02 (9H, s), 0.91+0.82 (3H, 2×t, J=7 Hz). Mass analysis: C43H50N2O6Si. Required: C, 71.84; H, 7.01; N, 3.90. Found: C, 71.54; H, 7.33; N, 3.88.

Provenance & Evidence