Sodium Hydroxide → 2-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-4-oxo-4-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-yl]-butyric Acid

HRID 494753Notes

Reaction equation

HRID 494753 reaction equation
[NH2:1][C:2]1[C:40]([C:41]([F:44])([F:43])[F:42])=[CH:39][C:5]([CH2:6][C:7]([CH2:18][C:19](=[O:38])[N:20]2[CH2:25][CH2:24][CH:23]([N:26]3[CH2:32][CH2:31][C:30]4[CH:33]=[CH:34][CH:35]=[CH:36][C:29]=4[NH:28][C:27]3=[O:37])[CH2:22][CH2:21]2)(C(OCC)=O)[C:8]([O:10]CC)=[O:9])=[CH:4][C:3]=1[Cl:45].[OH-].[Na+]>CCO.O>[NH2:1][C:2]1[C:40]([C:41]([F:43])([F:42])[F:44])=[CH:39][C:5]([CH2:6][CH:7]([CH2:18][C:19](=[O:38])[N:20]2[CH2:21][CH2:22][CH:23]([N:26]3[CH2:32][CH2:31][C:30]4[CH:33]=[CH:34][CH:35]=[CH:36][C:29]=4[NH:28][C:27]3=[O:37])[CH2:24][CH2:25]2)[C:8]([OH:10])=[O:9])=[CH:4][C:3]=1[Cl:45]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22184586Diethyl 2-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-2-{2-oxo-2-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-yl]-ethyl}-malonate2×

Product 1

HCID 221846012-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-4-oxo-4-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-yl]-butyric Acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 17.90 g (27.41 mmol) diethyl 2-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-2-{2-oxo-2-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-yl]-ethyl}-malonate (Intermediate product 67) in 1200 mL EtOH was added 5.48 g (137.00 mmol) NaOH in 500 mL water and the mixture was refluxed for 4 hours. EtOH was evaporated off i. vac. and the aqueous phase was acidified to pH 2 with conc. aqueous HCl. The precipitate formed was filtered off, washed with water and dried i. vac.

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. customEtOH was evaporated off i
  3. customThe precipitate formed
  4. filtrationwas filtered off
  5. washwashed with water
  6. customdried i

Sources & evidence

ORD record
ord-66f2f5be106549dfa696870bfabc7da5
Source dataset
uspto-grants-2009_05
Patent number
US07538115B2

Reaction notes

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