(5S)-1-{(2R)-2-(cyclopentylmethyl)-4-oxo-4-[(tetrahydro-2H-pyran-2-yloxy)amino]butanoyl}-N-2-pyrimidinyl-4,5-dihydro-1H-pyrazole-5-carboxamide → (5S)-1-[(2R)-2-(cyclopentylmethyl)-4-(hydroxyamino)-4-oxobutanoyl]-N-2-pyrimidinyl-4,5-dihydro-1H-pyrazole-5-carboxamide

Participants

Reaction Steps

A mixture of (5S)-1-{(2R)-2-(cyclopentylmethyl)-4-oxo-4-[(tetrahydro-2H-pyran-2-yloxy)amino]butanoyl}-N-2-pyrimidinyl-4,5-dihydro-1H-pyrazole-5-carboxamide (80 mg, 0.17 mmol) in acetic acid (8 mL) and water (2 mL) was stirred at room temperature for 3 days. The solvent was then removed to provide a residue which was purified by Gilson HPLC (Sunfire Column 19×50 mm, flowrate 25 mL/min, 10 min, 5-70% MeCN:H2O) to afford (5S)-1-[(2R)-2-(cyclopentylmethyl)-4-(hydroxyamino)-4-oxobutanoyl]-N-2-pyrimidinyl-4,5-dihydro-1H-pyrazole-5-carboxamide (24 mg, 35% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.15 (br. s., 2H) 1.37-1.94 (m, 9H) 2.41 (br. s., 1H) 2.64 (br. s., 1H) 3.24 (br. s., 2H) 3.52 (br. s., 1H) 3.83 (br. s., 1H) 5.11 (br. s., 1H) 6.99-7.07 (m, 2H) 8.64 (d, J=4.80 Hz, 2H) 9.21 (br. s., 1H) 10.33 (s, 1H).

Provenance & Evidence