Pyridine → (2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl fluoride

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To a solution of (2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoic acid (as prepared in Scheme 1; also described in WO 2009061879) (5.2 g, 17.03 mmol) dissolved in dichloromethane (DCM) (75 mL) was added 2,4,6-trifluoro-1,3,5-triazine (1.5 mL, 17.9 mmol) followed by pyridine (1.51 mL, 18.7 mmol). The reaction mixture was stirred at 25° C. for 2 h, and then the reaction mixture was diluted with DCM (100 mL) and washed (1×50 mL) with 5% citric acid followed by 50 mL of sat. NaHCO3. The organic layer was dried over magnesium sulfate, filtered, and concentrated to give (2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl fluoride as a pale yellow oil. LC-MS (ES) m/e 306.8 (M+H)+.

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