Sodium Hydroxide → 3-(4-Amino-3-chloro-5-trifluoromethyl-phenyl)-2-{[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-carbonyl]-amino}-propionic Acid

HRID 494750Notes

Reaction equation

HRID 494750 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([CH2:12][CH:13]([NH:19][C:20]([N:22]2[CH2:27][CH2:26][CH:25]([N:28]3[CH2:34][CH2:33][C:32]4[CH:35]=[CH:36][CH:37]=[CH:38][C:31]=4[NH:30][C:29]3=[O:39])[CH2:24][CH2:23]2)=[O:21])[C:14]([O:16]CC)=[O:15])=[CH:4][C:3]=1[Cl:40].[OH-].[Na+]>CCO>[NH2:1][C:2]1[C:7]([C:8]([F:10])([F:11])[F:9])=[CH:6][C:5]([CH2:12][CH:13]([NH:19][C:20]([N:22]2[CH2:23][CH2:24][CH:25]([N:28]3[CH2:34][CH2:33][C:32]4[CH:35]=[CH:36][CH:37]=[CH:38][C:31]=4[NH:30][C:29]3=[O:39])[CH2:26][CH2:27]2)=[O:21])[C:14]([OH:16])=[O:15])=[CH:4][C:3]=1[Cl:40]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22184546Ethyl 3-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-2-{[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-carbonyl]-amino}-propionate2×

Product 1

HCID 221846053-(4-Amino-3-chloro-5-trifluoromethyl-phenyl)-2-{[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-carbonyl]-amino}-propionic Acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 13.00 g (22.34 mmol) ethyl 3-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-2-{[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-carbonyl]-amino}-propionate (Intermediate product 59) in 100 mL EtOH was added 45 mL aqueous NaOH (1 M) and the mixture was stirred for 16 hours at RT. EtOH was evaporated i. vac., 45 mL aqueous HCl (1M) was added and 15 minutes stirred. The precipitate formed was filtered off, washed with water and dried i. vac. at 75° C.

Workup

  1. customEtOH was evaporated i
  2. addition, 45 mL aqueous HCl (1M) was added and 15 minutes
  3. stirringstirred
  4. customThe precipitate formed
  5. filtrationwas filtered off
  6. washwashed with water
  7. customdried i
  8. customat 75° C.

Sources & evidence

ORD record
ord-3c3f85dfbd5f4e409d5fca31e39f17ba
Source dataset
uspto-grants-2009_05
Patent number
US07538115B2

Reaction notes

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