Pyridine → (2R)-2-({formyl[(phenylmethyl)oxy]amino}methyl)heptanoyl fluoride

Participants

Reaction Steps

To a 250 mL round-bottomed flask was added (2R)-2-({formyl[(phenylmethyl)oxy]amino}methyl)heptanoic acid (WO 2003101442, also named (2R)-[(benzyloxyformylamino)methyl]heptanoic acid) (4.40 g, 15 mmol) in dichloromethane (60 mL), followed by pyridine (1.453 mL, 18.00 mmol) and 2,4,6-trifluoro-1,3,5-triazine (cyanuric fluoride) (2.168 g, 16.05 mmol). The reaction mixture was stirred at room temperature for 2 h, then was diluted with DCM, and washed with 5% Citric acid (150 mL) and sat. NaHCO3 (150 mL). The organic layer was dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography to provide (2R)-2-({formyl[(phenylmethyl)oxy]amino}methyl)heptanoyl fluoride as a colorless oil (1.88 g, 42%). LCMS: (M+H)+: 296.0.

Provenance & Evidence