phenylmethyl (3S)-3-{[(5-fluoro-2-pyridinyl)amino]carbonyl}-2-[(2R)-2-({formyl[(phenylmethyl)oxy]amino}methyl) heptanoyl]-1-pyrazolidinecarboxylate → (3S)-N-(5-fluoro-2-pyridinyl)-2-((2R)-2-{[formyl(hydroxy)amino]methyl}heptanoyl)-3-pyrazolidinecarboxamide

HRID 1396943Notes

Reaction equation

HRID 1396943 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C@@H:11]2[CH2:15][CH2:14][N:13](C(OCC3C=CC=CC=3)=O)[N:12]2[C:26](=[O:45])[C@@H:27]([CH2:33][N:34]([CH:43]=[O:44])[O:35]CC2C=CC=CC=2)[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[O:10])=[N:6][CH:7]=1>CO.[OH-].[OH-].[Pd+2]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C@@H:11]2[CH2:15][CH2:14][NH:13][N:12]2[C:26](=[O:45])[C@@H:27]([CH2:33][N:34]([CH:43]=[O:44])[OH:35])[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[O:10])=[N:6][CH:7]=1

Participants

4

Reactant 1

HCID 86706376phenylmethyl (3S)-3-{[(5-fluoro-2-pyridinyl)amino]carbonyl}-2-[(2R)-2-({formyl[(phenylmethyl)oxy]amino}methyl) heptanoyl]-1-pyrazolidinecarboxylate

Product 1

HCID 86706377(3S)-N-(5-fluoro-2-pyridinyl)-2-((2R)-2-{[formyl(hydroxy)amino]methyl}heptanoyl)-3-pyrazolidinecarboxamide

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a 100 mL round-bottomed flask was added phenylmethyl (3S)-3-{[(5-fluoro-2-pyridinyl)amino]carbonyl}-2-[(2R)-2-({formyl[(phenylmethyl)oxy]amino}methyl) heptanoyl]-1-pyrazolidinecarboxylate (696 mg, 1.123 mmol) in methanol (15 ml), followed by Pearlman's catalyst (120 mg). The mixture was stirred under a balloon of H2 for 80 min. The catalyst was filtered off, and the filtrate was concentrated to dryness to provide (3S)—N-(5-fluoro-2-pyridinyl)-2-((2R)-2-{[formyl(hydroxy)amino]methyl}heptanoyl)-3-pyrazolidinecarboxamide as a colorless oil. (420 mg, 94%). LCMS: (M+H)+: 396.0. 1H NMR (400 MHz, METHANOL-d4) δ ppm 0.75-1.00 (m, 3H) 1.16-1.39 (m, 6H) 1.47 (dd, J=8.59, 5.56 Hz, 1H) 1.52-1.68 (m, 1H) 2.02-2.31 (m, 1H) 2.49 (ddd, J=12.06, 6.25, 2.65 Hz, 1H) 2.86 (td, J=10.48, 6.06 Hz, 1H) 3.36 (br. s., 1H) 3.39-3.55 (m, 1H) 3.59-3.89 (m, 2H) 4.54-4.72 (m, 1H) 7.53 (ddd, J=9.16, 7.89, 3.16 Hz, 1H) 7.83 (s, 1H) 8.03-8.20 (m, 2H).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-edbb1ecf04714925a7d051641ca3487b
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

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