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

HRID 1396889Notes

Reaction equation

HRID 1396889 reaction equation
[CH:1]1([CH2:6][C@H:7]([CH2:26][N:27]([CH:36]=[O:37])[O:28]CC2C=CC=CC=2)[C:8]([N:10]2[C@H:14]([C:15]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][N:19]=3)=[O:16])[CH2:13][CH2:12][N:11]2[CH3:25])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1>CO.[OH-].[OH-].[Pd+2]>[CH:1]1([CH2:6][C@H:7]([CH2:26][N:27]([CH:36]=[O:37])[OH:28])[C:8]([N:10]2[C@H:14]([C:15]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][N:19]=3)=[O:16])[CH2:13][CH2:12][N:11]2[CH3:25])=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 86706353(3S)-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-N-(5-fluoro-2-pyridinyl)-1-methyl-3-pyrazolidinecarboxamide

Product 1

HCID 66548251(3S)-2-((2R)-3-cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)-N-(5-fluoro-2-pyridinyl)-1-methyl-3-pyrazolidinecarboxamideYield 57.9%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

(3S)-2-[(2R)-3-Cyclopentyl-2 ({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-N-(5-fluoro-2-pyridinyl)-1-methyl-3-pyrazolidinecarboxamide (84 mg, 0.164 mmol) was dissolved in methanol (9.66 ml). To this mixture was added 20% palladium hydroxide on carbon (23.06 mg, 0.033 mmol). The reaction mixture was degassed and placed under 1 atm of H2. After 2 h, the reaction mixture was filtered and concentrated. The residue was purified by RP-HPLC to afford (3S)-2-((2R)-3-cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)-N-(5-fluoro-2-pyridinyl)-1-methyl-3-pyrazolidinecarboxamide (40 mg, 0.095 mmol, 57.8% yield) as white foam solid. LC-MS (ES) m/e 422.1 (M+H)+.

Workup

  1. customThe reaction mixture was degassed
  2. filtrationthe reaction mixture was filtered
  3. concentrationconcentrated
  4. customThe residue was purified by RP-HPLC

Sources & evidence

ORD record
ord-bc32325585794e1d8e6e6644351c9972
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

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