HCID 53729834, compound → HCID 54355662, compound

HRID 1359033Notes

Reaction equation

HRID 1359033 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C@@H:16]2[CH2:21][CH2:20][N:19]([S:22]([C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=3)(=[O:24])=[O:23])[C@@H:18]([C:33](=[O:43])[NH:34][O:35]CC3C=CC=CC=3)[CH2:17]2)=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C@@H:16]2[CH2:21][CH2:20][N:19]([S:22]([C:25]3[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=3)(=[O:23])=[O:24])[C@@H:18]([C:33](=[O:43])[NH:34][OH:35])[CH2:17]2)=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 53729834HCID 53729834, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54355662HCID 54355662, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (2R,4R)-4-[2-benzyloxycarbamoyl-1-(4-methoxy-benzene-sulfonyl)-piperidine-4-carbonyl]-piperazine-1-carboxylic acid tert-butyl ester (500 mg, 0.81 mmol) and 5% palladium on barium sulfate (250 mg) in 10 mL of methanol was shaken under a 40 psi atmosphere of hydrogen gas for 1.5 hours. Filtration through nylon and concentration of the filtrate provided (2R,4R)-4-[2-hydroxycarbamoyl-1-(4-methoxy-benzenesulfonyl)-piperidine-4-carbonyl]-piperazine-1-carboxylic acid tert-butyl ester as a colorless solid, which was used in the subsequent step without purification.

Workup

  1. filtrationFiltration through nylon and concentration of the filtrate

Sources & evidence

ORD record
ord-3092de227cbe4a2ea11eea74cacc2e94
Source dataset
uspto-grants-2003_07
Patent number
US06599890B1

Reaction notes

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