4-Nitrophenol → 4-Nitropheny 3-[N-(2,4-diacetoxy 3,3-dimethyl-1-oxobutyl)amino]propionate

HRID 892875Notes

Reaction equation

HRID 892875 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[C:16]([O:19][CH:20]([C:29]([CH3:36])([CH3:35])[CH2:30][O:31][C:32](=[O:34])[CH3:33])[C:21]([NH:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])=[O:22])(=[O:18])[CH3:17].[CH:37]1[C:42]([N+:43]([O-:45])=[O:44])=[CH:41][CH:40]=[C:39](O)[CH:38]=1>O1CCCC1>[C:16]([O:19][CH:20]([C:29]([CH3:36])([CH3:35])[CH2:30][O:31][C:32](=[O:34])[CH3:33])[C:21]([NH:23][CH2:24][CH2:25][C:26]([O:28][C:39]1[CH:38]=[CH:37][C:42]([N+:43]([O-:45])=[O:44])=[CH:41][CH:40]=1)=[O:27])=[O:22])(=[O:18])[CH3:17]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 10868DicyclohexylcarbodiimideHCID 19893582HCID 19893582, compound

Product 1

HCID 198935384-Nitropheny 3-[N-(2,4-diacetoxy 3,3-dimethyl-1-oxobutyl)amino]propionateYield 32.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dicyclohexylcarbodiimide (15.5 g) was added to a solution of 22.6 g of 3-[N-(2,4-diacetoxy-3,3-dimethyl-1-oxobutyl)amino]propionic acid and 10.4 g of p-nitrophenol in 500 ml of tetrahydrofuran, and the mixture was stired for one night. After completion of the reaction, insoluble matter was removed and the solvent was distilled off under reduced pressure. The residue was dissolved in ethyl acetate. The resulting solution was washed with saturated aqueous sodium bicarbonate solution, with water and then with saturated saline, and dried over anhydrous sodium sulfate. After removing the solvent by evaporation, 10.2 g of the objectived compound was obtained as a residue (yield: 32%).

Workup

  1. waitthe mixture was stired for one night
  2. customAfter completion of the reaction, insoluble matter
  3. customwas removed
  4. distillationthe solvent was distilled off under reduced pressure
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washThe resulting solution was washed with saturated aqueous sodium bicarbonate solution, with water
  7. dry with materialwith saturated saline, and dried over anhydrous sodium sulfate
  8. customAfter removing the solvent
  9. customby evaporation

Sources & evidence

ORD record
ord-ce0fbb73cff5439e95bd61cd13853736
Source dataset
uspto-grants-1992_06
Patent number
US05120738

Reaction notes

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