(3S)-2-[(2R)-3-Cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-1-methyl-N-[3-(methyloxy)-2-pyrazinyl]-3-pyrazolidinecarboxamide → (3S)-2-((2R)-3-cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)-1-methyl-N-[3-(methyloxy)-2-pyrazinyl]-3-pyrazolidinecarboxamide

HRID 1396891Notes

Reaction equation

HRID 1396891 reaction equation
[CH:1]1([CH2:6][C@H:7]([CH2:27][N:28]([CH:37]=[O:38])[O:29]CC2C=CC=CC=2)[C:8]([N:10]2[C@H:14]([C:15]([NH:17][C:18]3[C:23]([O:24][CH3:25])=[N:22][CH:21]=[CH:20][N:19]=3)=[O:16])[CH2:13][CH2:12][N:11]2[CH3:26])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1>CO.[OH-].[OH-].[Pd+2]>[CH:1]1([CH2:6][C@H:7]([CH2:27][N:28]([CH:37]=[O:38])[OH:29])[C:8]([N:10]2[C@H:14]([C:15]([NH:17][C:18]3[C:23]([O:24][CH3:25])=[N:22][CH:21]=[CH:20][N:19]=3)=[O:16])[CH2:13][CH2:12][N:11]2[CH3:26])=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 86706354(3S)-2-[(2R)-3-Cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-1-methyl-N-[3-(methyloxy)-2-pyrazinyl]-3-pyrazolidinecarboxamide

Product 1

HCID 66548430(3S)-2-((2R)-3-cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)-1-methyl-N-[3-(methyloxy)-2-pyrazinyl]-3-pyrazolidinecarboxamideYield 56.8%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

(3S)-2-[(2R)-3-Cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-1-methyl-N-[3-(methyloxy)-2-pyrazinyl]-3-pyrazolidinecarboxamide (96 mg, 0.183 mmol) was dissolved in methanol (11 mL). To this mixture was added 20% palladium hydroxide on carbon (26.8 mg, 0.038 mmol). The reaction mixture was degassed and placed under 1 atm of H2. After 1 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)-1-methyl-N-[3-(methyloxy)-2-pyrazinyl]-3-pyrazolidinecarboxamide (45 mg, 0.104 mmol, 54.3% yield) as white foam solid. LC-MS (ES) m/e 435.4 (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-bcefc985cb7648f9a0a74ce6bd5baf84
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

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