phenylmethyl (3S)-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-3-[({2-[(3S)-3-(dimethylamino)-1-pyrrolidinyl]-4-pyrimidinyl}amino)carbonyl]-1-pyrazolidinecarboxylate → HCID 66546321, compound

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Reaction Steps

A mixture of phenylmethyl (3S)-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-3-[({2-[(3S)-3-(dimethylamino)-1-pyrrolidinyl]-4-pyrimidinyl}amino)carbonyl]-1-pyrazolidinecarboxylate (91 mg, 0.125 mmol) and Pearlman's catalyst (17.58 mg, 0.025 mmol) in methanol (7.4 ml) was degassed and placed under 1 atm of H2 at ambient temperature. After 2 hrs, the reaction mixture was filtered and concentrated to give a residue which was purified by RP-HPLC to give (3S)-2-((2R)-3-cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)-N-{2-[(3S)-3-(dimethylamino)-1-pyrrolidinyl]-4-pyrimidinyl}-3-pyrazolidinecarboxamide (45 mg, 0.089 mmol, 71% yield). MS (ES+) m/z 503.1 (MH+). 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.05-1.23 (m, 2H) 1.33-1.45 (m, 1H) 1.45-1.68 (m, 4H) 1.69-1.96 (m, 5H) 2.12-2.31 (m, 2H) 2.34 (s, 6H) 2.42-2.57 (m, 1H) 2.83-2.96 (m, 2H) 3.18-3.30 (m, 2H) 3.40-3.53 (m, 2H) 3.65-3.83 (m, 2H) 3.84-3.99 (m, 2H) 4.68 (q, J=7.16 Hz, 1H) 7.34 (d, J=5.56 Hz, 1H) 7.85 (s, 0.7H) 8.16 (d, J=5.81 Hz, 1H) 8.25 (s, 0.3H)

Provenance & Evidence