Ethyl Acetate → HCID 178475055, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (2R,3R,4S)-3-Acetylamino-4-[2,3-bis(tert-butoxycarbonyl)-guanidino]-3,4-dihydro-2H-pyran-2,6-dicarboxylic acid 6-benzhydryl ester (4.4 g) in dry dimethylformamide (10 ml) and pyridine (0.70 ml) was added pentafluorophenyl trifuoroacetate (1.27 ml) and the reaction was stirred at 23° C. for 1 hour. More pyridine (0.70 ml) and pentafluorophenyl trifluoroacetate (1.27 ml) was added and the reaction was stirred for a further 2 hours. The reaction mixture was diluted using ethyl acetate and washed consecutively using 1N hydrochloric acid, saturated sodium bicarbonate solution and brine. The organic phase was dired over anhydrous magnesium sulphate and the solvent was removed in vacuo to give the crude title compound as a tan foam, (8.11 g); 1H NMR (250MHz, D6 -DMSO) 9.97 (1H, broad s), 7.49--7.27 (11H, m), 6.91 (1H, s), 6.52 (1H, m), 4.93 (1H, m), 4.58 (1H, m), 4.47 (1H, m), 1.88 (3H,s), 1.42 (18H, s).

Provenance & Evidence