HCID 86706383, compound → HCID 66546694, compound

HRID 1396949Notes

Reaction equation

HRID 1396949 reaction equation
[CH:1]1([CH2:6][C@H:7]([CH2:33][N:34]([CH:43]=[O:44])[O:35]CC2C=CC=CC=2)[C:8]([N:10]2[C@H:14]([C:15]([NH:17][C:18]3[NH:19][CH:20]=[CH:21][N:22]=3)=[O:16])[CH2:13][CH2:12][N:11]2C(OCC2C=CC=CC=2)=O)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1>CO.[OH-].[OH-].[Pd+2]>[CH:1]1([CH2:6][C@H:7]([CH2:33][N:34]([CH:43]=[O:44])[OH:35])[C:8]([N:10]2[C@H:14]([C:15]([NH:17][C:18]3[NH:22][CH:21]=[CH:20][N:19]=3)=[O:16])[CH2:13][CH2:12][NH:11]2)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 86706383HCID 86706383, compound

Product 1

HCID 66546694HCID 66546694, compoundYield 93.5%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a 50 mL round-bottomed flask was added phenylmethyl (3S)-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-3-[(1H-imidazol-2-ylamino)carbonyl]-1-pyrazolidinecarboxylate (39 mg, 0.065 mmol) in methanol (3 ml), followed by Pearlman's catalyst (9 mg). The mixture was stirred under a balloon of H2 for 40 min, the catalyst was filtered off. Removal of the solvent provided (3S)-2-((2R)-3-cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)-N-1H-imidazol-2-yl-3-pyrazolidinecarboxamide as a off-white solid (23 mg, 92%). LCMS: (M+H)+: 379.4.

Workup

  1. filtrationthe catalyst was filtered off
  2. customRemoval of the solvent

Sources & evidence

ORD record
ord-630c1f5ec4ad488f8e129110894042cd
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

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