HCID 86706412, compound → HCID 86706411, compound

Participants

Reaction Steps

To a 500 ml round bottom flask under N2 was added (5S)-1-((2R)-2-(cyclopentylmethyl)-4-oxo-4-{[(phenylmethyl)oxy]amino}butanoyl)-N-2-pyridinyl-4,5-dihydro-1H-pyrazole-5-carboxamide (15.2 g, 31.8 mmol) in methanol (220 mL), followed by Pearlman's catalyst (3.17 g, 4.5 mmol). The mixture was degassed and hydrogenated using a H2 balloon. After 4 hours, LCMS indicated completion of the reaction. The mixture was kept under N2 in a refrigerator overnight. The clear solution on the top was decanted and filtered through 4 Acrodisc CR 25 mm Syringe Filters. The catalyst on the bottom was washed thoroughly with methanol (2×30 mL) and filtered. The combined filtrates were concentrated to dryness to provide (5S)-1-[(2R)-2-(cyclopentylmethyl)-4-(hydroxyamino)-4-oxobutanoyl]-N-2-pyridinyl-4,5-dihydro-1H-pyrazole-5-carboxamide (11.84 g, 30.6 mmol, 96% yield) as a white solid. 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.05-1.23 (m, 2H) 1.37-1.68 (m, 5H) 1.70-2.00 (m, 4H) 2.20-2.33 (m, 1H) 2.44 (d, J=9.09 Hz, 1H) 3.11-3.24 (m, 1H) 3.29-3.37 (m, 1H) 3.81-3.93 (m, 1H) 4.96-5.08 (m, 1H) 7.11 (s, 2H) 7.73-7.83 (m, 1H) 8.08 (d, J=8.34 Hz, 1H) 8.25-8.35 (m, 1H) 8.30 (d, J=4.80 Hz, 1H). LCMS: [M+H]+: 388.2.

Provenance & Evidence