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

HRID 902714Notes

Reaction equation

HRID 902714 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.Cl>CO.O.[OH-].[Na+]>[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 2

HCID 313Hydrochloric AcidHCID 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 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 14798Sodium HydroxideSolvent

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 mmole) in 10 mL of MeOH, 1 mL of H2O and 2 mL 2.5N NaOH was refluxed for 5 hours. 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 evaporated, and gave the titled compound, 172 mg (92% yield). MS (ESI) 625 (MH+).

Workup

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

Sources & evidence

ORD record
ord-2ba39fd97d1e414cb3bbbd6b5ed9e97b
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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