Sodium Hydroxide → 2-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-4-oxo-4-[4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidin-1-yl]-butanoic acid

HRID 736928Notes

Reaction equation

HRID 736928 reaction equation
[OH-].[Na+].[NH2:3][C:4]1[C:41]([C:42]([F:45])([F:44])[F:43])=[CH:40][C:7]([CH2:8][C:9]([CH2:20][C:21](=[O:39])[N:22]2[CH2:27][CH2:26][CH:25]([N:28]3[CH2:37][C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[NH:30][C:29]3=[O:38])[CH2:24][CH2:23]2)(C(OCC)=O)[C:10]([O:12]CC)=[O:11])=[CH:6][C:5]=1[Cl:46]>O.CCO>[NH2:3][C:4]1[C:41]([C:42]([F:44])([F:43])[F:45])=[CH:40][C:7]([CH2:8][CH:9]([CH2:20][C:21](=[O:39])[N:22]2[CH2:27][CH2:26][CH:25]([N:28]3[CH2:37][C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[NH:30][C:29]3=[O:38])[CH2:24][CH2:23]2)[C:10]([OH:12])=[O:11])=[CH:6][C:5]=1[Cl:46]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68592549diethyl 2-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-2-{2-oxo-2-[4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidin-1-yl]-ethyl}-malonate

Product 1

HCID 120944492-(4-amino-3-chloro-5-trifluoromethyl-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 962WaterSolvent

Procedure

3.13 g (78.25 mmol) of NaOH, dissolved in 300 mL water, were added to a solution of 10.00 g (15.65 mmol) of diethyl 2-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-2-{2-oxo-2-[4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidin-1-yl]-ethyl}-malonate in 600 mL EtOH and the mixture was refluxed for 4 h. EtOH was evaporated off i. vac., the reaction mixture was acidified to pH 1 with conc. HCl and 1 hour at RT. The precipitate formed was filtered off, washed with water and dried i. vac.

Workup

  1. temperaturethe mixture was refluxed for 4 h
  2. customEtOH was evaporated off i
  3. customwas acidified to pH 1 with conc. HCl and 1 hour at RT
  4. customThe precipitate formed
  5. filtrationwas filtered off
  6. washwashed with water
  7. customdried i

Sources & evidence

ORD record
ord-5795f8b28ec747d59bb97f18293d02ce
Source dataset
uspto-grants-2009_09
Patent number
US07595312B2

Reaction notes

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