Hydrochloric Acid → N-(2,2-Diphenylethyl)-N-(2-chloro-3-trifluoromethylbenzyl)-2,2-dimethyl-3-(3-aminopropoxy)phenylpropionic Acid

HRID 229122Notes

Reaction equation

HRID 229122 reaction equation
[C:1]1([CH:7]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH2:8][N:9]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:38])([F:37])[F:36])[C:30]=2[Cl:39])[CH2:10][CH2:11][CH2:12][O:13][C:14]2[C:15]([CH3:27])([CH3:26])[CH:16]([CH:20]([CH3:25])[C:21]([O:23]C)=[O:22])[CH:17]=[CH:18][CH:19]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].Cl>CO.O>[C:1]1([CH:7]([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH2:8][N:9]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:36])([F:37])[F:38])[C:30]=2[Cl:39])[CH2:10][CH2:11][CH2:12][O:13][C:14]2[C:15]([CH3:26])([CH3:27])[CH:16]([CH:20]([CH3:25])[C:21]([OH:23])=[O:22])[CH:17]=[CH:18][CH:19]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68863259methyl N-(2,2-diphenylethyl)-N-(2-chloro-3-trifluoromethylbenzyl)-2,2-dimethyl-3-(3-aminopropoxy)phenylpropionate

Product 1

HCID 68864466N-(2,2-Diphenylethyl)-N-(2-chloro-3-trifluoromethylbenzyl)-2,2-dimethyl-3-(3-aminopropoxy)phenylpropionic AcidYield 92%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A solution of methyl N-(2,2-diphenylethyl)-N-(2-chloro-3-trifluoromethylbenzyl)-2,2-dimethyl-3-(3-aminopropoxy)phenylpropionate (195 mg, 0.3 mmol) in MeOH (10 mL), H2O (1 mL), and 2.5N NaOH (2 mL) was refluxed for 5 h. The reaction was cooled, diluted with H2O, and acidified with 3N HCl to pH=5.1. The mixture was extracted with EtOAc, the extracts were washed with H2O, dried, and concentrated to yield the titled compound (172 mg, 92%). MS (ESI) 625 (M+H+).

Workup

  1. temperatureThe reaction was cooled
  2. extractionThe mixture was extracted with EtOAc
  3. washthe extracts were washed with H2O
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2bff7b9c447a4dd898cad5fea9026c98
Source dataset
uspto-grants-2009_07
Patent number
US07560586B2

Reaction notes

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