Acetic Acid → (5S)-1-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-4,5-dihydro-1H-pyrazole-5-carboxylic acid

Participants

Reaction Steps

4,5-Dihydro-1H-pyrazole-5-carboxylic acid (1.273 g, 11.16 mmol) in 26.6 mL of DCM was added into a solution of (2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl fluoride (4.12 g, 13.39 mmol) in 30 mL of DCM, and followed by Hunig's base (5.83 ml, 33.5 mmol). The resulting solution was stirred at ambient temperature for 2 hrs. HOAc (10 ml) was added to neutralize the solution, and then the solvent was removed to give a crude product which was purified by RP-HPLC to give (5S)-1-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-4,5-dihydro-1H-pyrazole-5-carboxylic acid (1.03 g, 2.57 mmol, 46% yield). MS (ES+) m/z 401.9 (MH+).

Provenance & Evidence