Sodium Hydroxide → HCID 68864364, compound

HRID 229118Notes

Reaction equation

HRID 229118 reaction equation
[C:1]1([CH:7]([CH:37]2[CH2:41][CH2:40][CH2:39][CH2:38]2)[CH2:8][N:9]([CH2:22][CH2:23][CH2:24][O:25][C:26]2[CH2:27][C:28](=[CH:32][C:33]([O:35]C)=[O:34])[CH:29]=[CH:30][CH:31]=2)[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[C:12]=2[Cl:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>CO.C1COCC1.O>[C:1]1([CH:7]([CH:37]2[CH2:41][CH2:40][CH2:39][CH2:38]2)[CH2:8][N:9]([CH2:22][CH2:23][CH2:24][O:25][C:26]2[CH2:27][C:28](=[CH:32][C:33]([OH:35])=[O:34])[CH:29]=[CH:30][CH:31]=2)[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:18])([F:20])[F:19])[C:12]=2[Cl:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 68864032HCID 68864032, compound

Product 1

HCID 68864364HCID 68864364, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-(2-phenyl-2-cyclopentylethyl)-N-(2-chloro-3-trifluoromethylbenzyl)-3-(3-carbomethoxymethylenephenoxy)propylamine (159 mg, 0.27 mmol) in MeOH (5 mL), THF (1 mL), H2O (1 mL), and 2.5 N NaOH (2.5 mL) was heated to 50° C. for 1 h. The reaction was cooled, diluted with H2O, acidified to pH=5.5, and extracted with EtOAc. The extracts were washed with H2O, dried, and concentrated to yield the titled compound (93 mg, 70%). MS (ESI) 575 (M+H+).

Workup

  1. temperatureThe reaction was cooled
  2. extractionextracted with EtOAc
  3. washThe extracts were washed with H2O
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-60c61610f06647aab3cd31be89468a49
Source dataset
uspto-grants-2009_07
Patent number
US07560586B2

Reaction notes

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