Water → HCID 178523980, compound

HRID 1396882Notes

Reaction equation

HRID 1396882 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([NH:10][C:11]([C@@H:13]3[CH2:17][CH2:16][N:15](C(OCC4C=CC=CC=4)=O)[N:14]3[C:28](=[O:48])[C@@H:29]([CH2:36][N:37]([CH:46]=[O:47])[O:38]CC3C=CC=CC=3)[CH2:30][CH:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)=[O:12])=[CH:9][C:4]=2[N:3]=[N:2]1.O>CO.[OH-].[OH-].[Pd+2]>[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([NH:10][C:11]([C@@H:13]3[CH2:17][CH2:16][NH:15][N:14]3[C:28](=[O:48])[C@@H:29]([CH2:36][N:37]([CH:46]=[O:47])[OH:38])[CH2:30][CH:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)=[O:12])=[CH:9][C:4]=2[N:3]=[N:2]1

Participants

5

Reactant 2

HCID 962WaterHCID 178523395HCID 178523395, compound

Product 1

HCID 178523980HCID 178523980, compoundYield 75.9%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of phenylmethyl (3S)-3-[(1H-1,2,3-benzotriazol-5-ylamino)carbonyl]-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-1-pyrazolidinecarboxylate (87.2 mg, 0.133 mmol) in methanol (2.7 ml) was added 20% palladium hydroxide on carbon, 50% water (18.73 mg, 0.133 mmol). The mixture was hydrogenated under balloon pressure for 3 h, and was then filtered through a 0.2 μm PTFE membrane. The solution was concentrated in vacuo, and the residue was azeotroped with EtOAc (10 mL). The residue was triturated with 30% EtOAc in hexanes, and the solid was collected by vacuum filtration to give (3S)—N-1H-1,2,3-benzotriazol-5-yl-2-((2R)-3-cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)-3-pyrazolidinecarboxamide (43.2 mg, 0.101 mmol, 75% yield) as a white solid. LC/MS: (M+H)+: 430.1.

Workup

  1. filtrationwas then filtered through a 0.2 μm PTFE membrane
  2. concentrationThe solution was concentrated in vacuo
  3. customthe residue was azeotroped with EtOAc (10 mL)
  4. customThe residue was triturated with 30% EtOAc in hexanes
  5. filtrationthe solid was collected by vacuum filtration

Sources & evidence

ORD record
ord-1dde217ce58e43ada120d7ecbb12c26a
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

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