Hydrochloric Acid → 1-(2-{2-Chloro-4-[2-(2-chloro-4-trifluoromethyl-phenoxy)-acetylamino]-phenoxy}-ethyl)-piperidin-4-carboxylic acid

HRID 898598Notes

Reaction equation

HRID 898598 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:23]=[C:22]([NH:24][C:25](=[O:39])[CH2:26][O:27][C:28]2[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][C:29]=2[Cl:38])[CH:21]=[CH:20][C:5]=1[O:6][CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][CH:12]([C:15]([O:17]CC)=[O:16])[CH2:11][CH2:10]1.Cl>CCO>[Cl:3][C:4]1[CH:23]=[C:22]([NH:24][C:25](=[O:39])[CH2:26][O:27][C:28]2[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:35])[F:36])=[CH:30][C:29]=2[Cl:38])[CH:21]=[CH:20][C:5]=1[O:6][CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][CH:12]([C:15]([OH:17])=[O:16])[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 9985339Ethyl 1-(2-{2-chloro-4-[2-(2-chloro-4-trifluoromethyl-phenoxy)-acetylamino]-phenoxy}-ethyl)-piperidine4-carboxylate

Product 1

HCID 596916001-(2-{2-Chloro-4-[2-(2-chloro-4-trifluoromethyl-phenoxy)-acetylamino]-phenoxy}-ethyl)-piperidin-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2 mL aqueous NaOH (1 M) was added at RT to a solution of 150 mg (0.270 mmol) ethyl 1-(2-{2-chloro-4-[2-(2-chloro-4-trifluoromethyl-phenoxy)-acetylamino]-phenoxy}-ethyl)-piperidine-4-carboxylate (Example 146) in 4 mL EtOH and the mixture was stirred for 16 h. The reaction mixture was neutralised with 2 mL aqueous HCl (1 M), evaporated down i. vac. and the crude product was purified by column chromatography (silica gel, dichloromethane/MeOH 4:1).

Workup

  1. customevaporated down i
  2. customand the crude product was purified by column chromatography (silica gel, dichloromethane/MeOH 4:1)

Sources & evidence

ORD record
ord-974ca5b0083845f9a33c2f2436eb794b
Source dataset
uspto-grants-2008_04
Patent number
US07351719B2

Reaction notes

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