Dimethylformamide → 5-t-Butoxycarbonylamino-2-hydroxybenzoic acid 4-(nitrooxy)butyl ester

HRID 2240615Notes

Reaction equation

HRID 2240615 reaction equation
CN(C=O)C.[C:6]([O:10][C:11]([NH:13][C:14]1[CH:22]=[C:18]([C:19]([OH:21])=[O:20])[C:17]([OH:23])=[CH:16][CH:15]=1)=[O:12])([CH3:9])([CH3:8])[CH3:7].C1(C)C=CC(S(O[CH2:34][CH2:35][CH2:36][CH2:37][O:38][N+:39]([O-:41])=[O:40])(=O)=O)=CC=1>O>[N+:39]([O:38][CH2:37][CH2:36][CH2:35][CH2:34][O:20][C:19](=[O:21])[C:18]1[CH:22]=[C:14]([NH:13][C:11]([O:10][C:6]([CH3:9])([CH3:7])[CH3:8])=[O:12])[CH:15]=[CH:16][C:17]=1[OH:23])([O-:41])=[O:40]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 103775625-(N-tert-Butoxycarbonylamino)salicylic AcidHCID 184487104-Nitrooxybutyl p-toluenesulfonate

Product 1

HCID 684906975-t-Butoxycarbonylamino-2-hydroxybenzoic acid 4-(nitrooxy)butyl esterYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture comprising DMF (200 ml), 5-t-butoxycarbonylaminosalicylic acid (4.37 g, 17.3 mmol) and 4-nitrooxybutyl p-toluenesulfonate (5 g, 17.3 mmol), at room temperature and under stirring triethylamine was added (2,6 ml; 19 mmol). The reaction mixture was maintained 3 days under stirring at room temperature. It was then poured in water and extracted with ethyl ether. The combined organic phases were washed with a sodium carbonate solution and then with water. After drying on sodium sulfate, the evaporation of the solvent yields a raw product that purified by silica gel chromatography gives the title compounds with a yield of 65%.

Workup

  1. temperatureThe reaction mixture was maintained 3 days
  2. extractionextracted with ethyl ether
  3. washThe combined organic phases were washed with a sodium carbonate solution
  4. customAfter drying on sodium sulfate
  5. customthe evaporation of the solvent
  6. customyields a raw product
  7. customthat purified by silica gel chromatography

Sources & evidence

ORD record
ord-3730a7e5e17641e5b3c5d6165847ce63
Source dataset
uspto-grants-2010_05
Patent number
US07723382B2

Reaction notes

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