Potassium Hydroxide → 2-(3,4-dimethyl-benzyl)-4-oxo-4-[4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidin-1-yl]-butanoic acid

HRID 644367Notes

Reaction equation

HRID 644367 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:37]=[CH:38][C:39]=1[CH3:40])[CH2:5][C:6]([CH2:17][C:18](=[O:36])[N:19]1[CH2:24][CH2:23][CH:22]([N:25]2[CH2:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[NH:27][C:26]2=[O:35])[CH2:21][CH2:20]1)(C(OCC)=O)[C:7]([O:9]CC)=[O:8].[OH-].[K+]>CCO.O>[CH3:1][C:2]1[CH:3]=[C:4]([CH:37]=[CH:38][C:39]=1[CH3:40])[CH2:5][CH:6]([CH2:17][C:18](=[O:36])[N:19]1[CH2:24][CH2:23][CH:22]([N:25]2[CH2:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[NH:27][C:26]2=[O:35])[CH2:21][CH2:20]1)[C:7]([OH:9])=[O:8]

Participants

5

Reactant 2

HCID 14797Potassium Hydroxide2×HCID 68579159diethyl 2-(3,4-dimethyl-benzyl)-2-{2-oxo-2-[4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidin-1-yl]-ethyl}-malonate

Product 1

HCID 685810572-(3,4-dimethyl-benzyl)-4-oxo-4-[4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidin-1-yl]-butanoic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent3×

Procedure

A solution of 15.5 g (28.2 mmol) diethyl 2-(3,4-dimethyl-benzyl)-2-{2-oxo-2-[4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidin-1-yl]-ethyl}-malonate in 100 mL EtOH was combined with 11.2 g (169.7 mmol) KOH dissolved in 150 mL water and the mixture was refluxed for 5 h. After the addition of another 11.2 g (169.7 mmol) KOH dissolved in 150 mL water the mixture was refluxed again for 5 h, then combined with 150 mL water and the precipitate was suction filtered. The filter cake was dissolved in 500 mL water, washed twice with 100 mL EtOAc and adjusted to pH 4 by the addition of conc. HCl. The precipitate formed was suction filtered and dried in the circulating air dryer.

Workup

  1. temperaturethe mixture was refluxed for 5 h
  2. temperaturewas refluxed again for 5 h
  3. filtrationfiltered
  4. dissolutionThe filter cake was dissolved in 500 mL water
  5. washwashed twice with 100 mL EtOAc
  6. additionadjusted to pH 4 by the addition of conc. HCl
  7. customThe precipitate formed
  8. filtrationfiltered
  9. customdried in the circulating air dryer

Sources & evidence

ORD record
ord-afcc51205e2942728b9cea1e06f65caa
Source dataset
uspto-grants-2010_04
Patent number
US07700589B2

Reaction notes

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