phenylmethyl (3S)-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-3-[(4-pyrimidinylamino)carbonyl]-1-pyrazolidinecarboxylate → (3S)-2-((2R)-3-cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)-N-4-pyrimidinyl-3-pyrazolidinecarboxamide

Beteiligte Stoffe

Reaktionsschritte

A mixture of phenylmethyl (3S)-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-3-[(4-pyrimidinylamino)carbonyl]-1-pyrazolidinecarboxylate (4.22 g, 6.87 mmol) and Pearlman's catalyst (964 mg, 1.37 mmol) in methanol (381 mL) was degassed and placed under 1 atm of H2 at 25° C. After 2 hrs, the reaction mixture was filtered and concentrated to give a crude residue which was purified by RP-HPLC to provide (3S)-2-((2R)-3-cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)-N-4-pyrimidinyl-3-pyrazolidinecarboxamide as a foamy solid (1.8 g, 67% yield). The material was dissolved and evaporated from acetonitrile (2×5 mL) to provide a white solid. MS (ES+) m/z 391.2 (MH+). 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.06-1.23 (m, 2H) 1.34-1.47 (m, 1H) 1.47-1.67 (m, 4H) 1.69-1.97 (m, 4H) 2.15-2.29 (m, 1H) 2.45-2.60 (m, 1H) 2.85-2.99 (m, 1H) 3.20-3.28 (m, 1H) 3.49 (dd, J=13.89, 4.55 Hz, 1H) 3.59-3.85 (m, 1H) 3.94 (dt, J=9.41, 4.77 Hz, 1H) 4.64-4.74 (m, 1H) 7.86 (s, 0.7H) 8.17 (dd, J=6.06, 1.26 Hz, 1H) 8.25 (s, 0.3H) 8.60 (d, J=6.06 Hz, 1H) 8.82 (s, 1H).

Herkunft & Nachweise