4-Aminophenol → 2,4-Diacetoxy-N-[3-[(4-hydroxyphenyl)amino]-3-oxopropyl]-3,3-dimethylbutanamide

HRID 892879Notes

Reaction equation

HRID 892879 reaction equation
C(N=C=NCCCN(C)C)C.[C:12]([O:15][CH:16]([C:25]([CH3:32])([CH3:31])[CH2:26][O:27][C:28](=[O:30])[CH3:29])[C:17]([NH:19][CH2:20][CH2:21][C:22]([OH:24])=O)=[O:18])(=[O:14])[CH3:13].[CH:33]1[C:38]([NH2:39])=[CH:37][CH:36]=[C:35]([OH:40])[CH:34]=1>C(Cl)Cl>[C:12]([O:15][CH:16]([C:25]([CH3:32])([CH3:31])[CH2:26][O:27][C:28](=[O:30])[CH3:29])[C:17]([NH:19][CH2:20][CH2:21][C:22]([NH:39][C:38]1[CH:33]=[CH:34][C:35]([OH:40])=[CH:36][CH:37]=1)=[O:24])=[O:18])(=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 4034-AminophenolHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 19893582HCID 19893582, compound

Product 1

HCID 198936262,4-Diacetoxy-N-[3-[(4-hydroxyphenyl)amino]-3-oxopropyl]-3,3-dimethylbutanamideYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide (2.30 g) was added to a solution of 3.03 g of 3-[N-(2,4-diacetoxy-3,3-dimethyl-1-oxobutyl)amino]propionic acid and 2.18 g of p-aminophenol in 50 ml of methylene chloride, and the mixture was stirred for one night. After completion of the reaction, the reaction mixture was washed with water, and dried over anhydrous sodium sulfate. After removing the solvent by evaporation, the residue obtained was purified by silica gel column chromatography to obtain 1.92 g of the objective compound was obtained as a residue (yield: 50%).

Workup

  1. customAfter completion of the reaction
  2. washthe reaction mixture was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customAfter removing the solvent
  5. customby evaporation
  6. customthe residue obtained
  7. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-29ebae54edf34cfdbcc7eb7763d0fa8a
Source dataset
uspto-grants-1992_06
Patent number
US05120738

Reaction notes

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