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

HRID 275837Notes

Reaction equation

HRID 275837 reaction equation
[CH3:1][N:2]([O:23][CH3:24])[C:3](=[O:22])[C:4]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:5]=1[NH:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13].[CH:25](I)([CH3:27])[CH3:26].[C:29](=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:1][N:2]([O:23][CH3:24])[C:3](=[O:22])[C:4]1[CH:9]=[C:8]([O:10][CH2:26][CH:25]([CH3:27])[CH3:29])[CH:7]=[CH:6][C:5]=1[NH:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 18315375N-methyl-N-methyloxy-2-benzyloxycarbonylamino-5-hydroxybenzamide

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-methyl-N-methyloxy-2-benzyloxycarbonylamino-5-hydroxybenzamide (3.0 g), isopropyl iodide (2.2 g) and potassium carbonate (2.0 g) in N,N-dimethylformamide (20 ml) was stirred for 15 hours at 70° C. To the reaction mixture was added water, which was subjected to extraction with ethyl acetate (80 ml). The organic layer was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by means of a silica gel column chromatography to give N-methyl-N-methyloxy-2-benzyloxycarbonylamino-5-isobutyloxybenzamide.as an orange oily product (1.0 g).

Workup

  1. extractionwas subjected to extraction with ethyl acetate (80 ml)
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off
  5. customthe residue was purified by means of a silica gel column chromatography

Sources & evidence

ORD record
ord-42ee668c66c54ecca5a8a6bf9f2152ae
Source dataset
uspto-grants-2002_03
Patent number
US06352982B1

Reaction notes

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