(3S)-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-1-methyl-N-4-pyrimidinyl-3-pyrazolidinecarboxamide → (3S)-2-((2R)-3-cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)-1-methyl-N-4-pyrimidinyl-3-pyrazolidinecarboxamide

HRID 1396887Notes

Reaction equation

HRID 1396887 reaction equation
[CH:1]1([CH2:6][C@H:7]([CH2:25][N:26]([CH:35]=[O:36])[O:27]CC2C=CC=CC=2)[C:8]([N:10]2[C@H:14]([C:15]([NH:17][C:18]3[CH:23]=[CH:22][N:21]=[CH:20][N:19]=3)=[O:16])[CH2:13][CH2:12][N:11]2[CH3:24])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1>CO.[OH-].[OH-].[Pd+2]>[CH:1]1([CH2:6][C@H:7]([CH2:25][N:26]([CH:35]=[O:36])[OH:27])[C:8]([N:10]2[C@H:14]([C:15]([NH:17][C:18]3[CH:23]=[CH:22][N:21]=[CH:20][N:19]=3)=[O:16])[CH2:13][CH2:12][N:11]2[CH3:24])=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 86706352(3S)-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-1-methyl-N-4-pyrimidinyl-3-pyrazolidinecarboxamide

Product 1

HCID 66548081(3S)-2-((2R)-3-cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)-1-methyl-N-4-pyrimidinyl-3-pyrazolidinecarboxamideYield 71.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

(3S)-2-[(2R)-3-Cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-1-methyl-N-4-pyrimidinyl-3-pyrazolidinecarboxamide (120 mg, 0.243 mmol) was dissolved in methanol (14 mL). To this mixture was added palladium hydroxide on carbon (34.1 mg, 0.049 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)-1-methyl-N-4-pyrimidinyl-3-pyrazolidinecarboxamide (70 mg, 0.173 mmol, 71.3% yield) as white foam solid. LC-MS (ES) m/e 405.3 (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-69c4ddf190bd462eab1f8b9ba78ec56d
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

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