3-(4-Methoxybenzylamino)-5-chloro-6-methyl-1-benzyloxycarbonylmethyl-pyrazinone → 3-(4-Methoxybenzylamino)-5-chloro-6-methyl-1-carboxymethylpyrazinone

HRID 322545Notes

Reaction equation

HRID 322545 reaction equation
[CH3:1][O:2][C:3]1[CH:30]=[CH:29][C:6]([CH2:7][NH:8][C:9]2[C:10](=[O:28])[N:11]([CH2:17][C:18]([O:20]CC3C=CC=CC=3)=[O:19])[C:12]([CH3:16])=[C:13]([Cl:15])[N:14]=2)=[CH:5][CH:4]=1>C1(C)C=CC=CC=1.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][NH:8][C:9]2[C:10](=[O:28])[N:11]([CH2:17][C:18]([OH:20])=[O:19])[C:12]([CH3:16])=[C:13]([Cl:15])[N:14]=2)=[CH:29][CH:30]=1

Participants

4

Reactant 1

HCID 220087883-(4-Methoxybenzylamino)-5-chloro-6-methyl-1-benzyloxycarbonylmethyl-pyrazinone

Product 1

HCID 220087753-(4-Methoxybenzylamino)-5-chloro-6-methyl-1-carboxymethylpyrazinone

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

A solution of the benzyl ester 18-4 (1.06 g, 2.48 mmol) in toluene (60 mL) was degassed with argon and then 150 mg 10% palladium on carbon was added. The mixture was stirred under an atmosphere of hydrogen gas for 16 h. The solution was filtered through celite and the solvent evaporated to give the title compound 18-5 as a white solid:

Workup

  1. filtrationThe solution was filtered through celite
  2. customthe solvent evaporated

Sources & evidence

ORD record
ord-4115e3399868401f87fd1613c9b68ec3
Source dataset
uspto-grants-2001_04
Patent number
US06211184B1

Reaction notes

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