Sodium Hydroxide → HCID 22479280, compound

HRID 1017463Notes

Reaction equation

HRID 1017463 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[CH3:24])[C:15]([C:25](=[O:43])[N:26]([CH2:28][C:29]3[CH:34]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:32]=[C:31]([C:39]([F:42])([F:41])[F:40])[CH:30]=3)[CH3:27])=[CH:14][N:13]=2)[CH2:8][CH2:7]1)=[O:5])C.[OH-].[Na+]>CO>[F:42][C:39]([F:40])([F:41])[C:31]1[CH:30]=[C:29]([CH:34]=[C:33]([C:35]([F:36])([F:37])[F:38])[CH:32]=1)[CH2:28][N:26]([CH3:27])[C:25]([C:15]1[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[CH3:24])=[CH:17][C:12]([N:9]2[CH2:8][CH2:7][CH:6]([C:4]([OH:5])=[O:3])[CH2:11][CH2:10]2)=[N:13][CH:14]=1)=[O:43]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86585484HCID 86585484, compound

Product 1

HCID 22479280HCID 22479280, compoundYield 42.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 200 mg (0.33 mmol) 5′-[(3,5-bis-trifluoromethyl-benzyl)-methyl-carbamoyl]-4′-o-tolyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-carboxylic acid ethyl ester (Example 45), 10 ml 1N aqueous sodium hydroxide solution and 10 ml methanol was stirred at room temperature over night. After washing with 2 portions of ethyl acetate the aqueous layer was acidified to pH 4 with 1N aqueous hydrochloric acid solution. Extraction with dichloromethane, drying with sodium sulfate and flash column chromatography afforded 81 mg (42%) of the title compound as a white solid.

Workup

  1. washAfter washing with 2 portions of ethyl acetate the aqueous layer
  2. extractionExtraction with dichloromethane
  3. dry with materialdrying with sodium sulfate and flash column chromatography

Sources & evidence

ORD record
ord-a797f08deb924c919c69ed0459d35ab4
Source dataset
uspto-grants-2002_11
Patent number
US06479483B2

Reaction notes

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