Pyridine → HCID 10676004, compound

Participants

Reaction Steps

(2R,3R,4S)-3-Acetylamino-4-(tert-butoxycarbonylamino)-3,4-dihydro-2H-pyran-2,6-dicarboxylic acid 6-benzhydryl ester (3.36 g) was dissolved in dry dimethylformamide (10 ml) and pyridine (0.632 g) under nitrogen and stirred at 23° C. To this was added pentafluorophenyl trifluoroacetate (2.02 g). After 3 hours the reaction mixture was diluted with ethyl acetate (250 ml) and washed with dilute hydrochloric acid (3×50 ml), dilute sodium bicarbonate solution (3×50 ml) and brine (50 ml). The organic phase was dried over anhydrous magnesium sulphate and the solvent was removed in vacuo to give the title compound as an off-white foam. (4.353 g); 1H NMR (250 MHz, DMSO) 8.22 (1H, d, J=8Hz), 7.50-7.27 (10H, m), 7.06 (1H, m), 6.94 (1H, s), 6.18 (1H, d, J=3.8Hz), 5.25 (1H, d, J=6.8Hz), 4.42 (1H, m), 4.29 (1H, m), 1.82 (3H, s), 1.38 (9H, s).

Provenance & Evidence