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

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Reaction Steps

4,5-Dihydro-1H-pyrazole-5-carboxylic acid (939 mg, 8.23 mmol) in 20 ml of DCM was added into a solution of (2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl fluoride (3035 mg, 9.88 mmol) in 21.8 ml of DCM, and followed by Hunig's base (4.3 ml, 24.69 mmol). The resulting solution was stirred at ambient temperature for 1 hr. HOAc (8 ml) was added to neutralize the solution, and then it 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 (660 mg, 1.644 mmol, 40% yield). MS (ES+) m/z 401.9 (MH+).

Provenance & Evidence