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

HRID 1396962Notes

Reaction equation

HRID 1396962 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:44])[C@@H:27]([CH2:32][N:33]([CH:42]=[O:43])[O:34]CC2C=CC=CC=2)[CH2:28][CH2:29][CH2:30][CH3:31])=[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:44])[C@@H:27]([CH2:32][N:33]([CH:42]=[O:43])[OH:34])[CH2:28][CH2:29][CH2:30][CH3:31])=[O:10])=[N:6][CH:7]=1

Participants

4

Reactant 1

HCID 86706393Phenylmethyl (3S)-3-{[(5-fluoro-2-pyridinyl)amino]carbonyl}-2-[(2R)-2-({formyl[(phenylmethyl)oxy]amino}methyl)hexanoyl]-1-pyrazolidinecarboxylate

Product 1

HCID 88948336(3S)-N-(5-fluoro-2-pyridinyl)-2-((2R)-2-{[formyl(hydroxy)amino]methyl}hexanoyl)-3-pyrazolidinecarboxamideYield 48%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of phenylmethyl (3S)-3-{[(5-fluoro-2-pyridinyl)amino]carbonyl}-2-[(2R)-2-({formyl[(phenylmethyl)oxy]amino}methyl)hexanoyl]-1-pyrazolidinecarboxylate (230 mg, 0.38 mmol) in methanol (30 mL) was added Pd(OH)2/C (230 mg). The mixture was degassed and then stirred under an H2 atmosphere for 3 h at rt. The catalyst was filtered off. The filtrate was concentrated and the residue was purified by pre-HPLC to provide the title compound (67 mg, 48%). LCMS: (M+H)+: 382.2.

Workup

  1. customThe mixture was degassed
  2. filtrationThe catalyst was filtered off
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified by pre-HPLC

Sources & evidence

ORD record
ord-41465286860249c6a855c2712a35f045
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

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