N-methyl-N-methyloxy-2-benzyloxycarbonylamino-5-isobutyloxybenzamide → N-methyl-N-methyloxy-2-amino-5-isobutyloxybenzamide

HRID 275838Notes

Reaction equation

HRID 275838 reaction equation
[CH3:1][N:2]([O:27][CH3:28])[C:3](=[O:26])[C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH:12]([CH3:14])[CH3:13])[CH:7]=[CH:6][C:5]=1[NH:15]C(OCC1C=CC=CC=1)=O>C(OCC)(=O)C.CO.[C].[Pd]>[CH3:1][N:2]([O:27][CH3:28])[C:3](=[O:26])[C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH:12]([CH3:14])[CH3:13])[CH:7]=[CH:6][C:5]=1[NH2:15]

Participants

5

Reactant 1

HCID 18315337N-methyl-N-methyloxy-2-benzyloxycarbonylamino-5-isobutyloxybenzamide

Product 1

HCID 18315340N-methyl-N-methyloxy-2-amino-5-isobutyloxybenzamide

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-Methyl-N-methyloxy-2-benzyloxycarbonylamino-5-isobutyloxybenzamide (1.0 g) was dissolved in a mixture of ethyl acetate (10 ml) and methanol (10 ml). To the solution was added 10% palladium-carbon (0.2 g). The mixture was stirred for two hours at room temperature under hydrogen atmosphere. The reaction mixture was subjected to filtration. From the filtrate, the solvent was distilled off to leave N-methyl-N-methyloxy-2-amino-5-isobutyloxybenzamide as a yellow oily product (0.6 g).

Workup

  1. filtrationThe reaction mixture was subjected to filtration
  2. distillationFrom the filtrate, the solvent was distilled off

Sources & evidence

ORD record
ord-5518739afb344fd08d0a4a2f9d51b659
Source dataset
uspto-grants-2002_03
Patent number
US06352982B1

Reaction notes

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