1,2-Dichloroethane → 5-Fluoro-4-hydroxy-3-[1-(benzyloxycarbonyl)-2-piperidinecarboxamido]-pentanoic acid tert-butyl ester

Participants

Reaction Steps

A stirred mixture of (S)-1-(benzyloxy carbonyl)-2-piperidinecarboxylic acid (4.82 g, 18.31 mmol), 3-amino-5-fluoro-4-hydroxy-pentanoic acid tert-butyl ester (3.99 g, 19.25 mmol), HOBt (2.72 g, 20.13 mmol), DMAP (2.57 g, 21.04 mmol) and anhydrous THF (60 ml) was cooled to 0° C. before EDC (3.86 g, 20.13 mmol) was added. The mixture was allowed to warm to room temperature over 16 hrs before being concentrated under reduced pressure. The residue was purified by flash chromatography (60% ethyl acetate in hexane) to afford the sub-title compound as a white foam (7.3754 g, 72%): 1H NMR (400 MHz, CDCl3) δ 1.31-1.80 (14H, m), 2.20-2.38 (1H, m), 2.49-3.07 (3H, m), 3.11-3.70 (1H, m), 3.80-4.58 (4H, m), 4.70-5.28 (1H, m), 6.58-7.05 (1H, m), 7.23-7.48 (5H, m).

Provenance & Evidence