Methanol → HCID 23502847, compound

HRID 1835347Notes

Reaction equation

HRID 1835347 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])[C:8]([C:18](=[O:36])[N:19]([CH2:21][C:22]2[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[C:24]([C:32]([F:35])([F:34])[F:33])[CH:23]=2)[CH3:20])=[CH:7][N:6]=1)=[O:4].CO.O1CCOCC1.[OH-].[Na+]>O>[F:30][C:28]([F:29])([F:31])[C:26]1[CH:27]=[C:22]([CH:23]=[C:24]([C:32]([F:35])([F:34])[F:33])[CH:25]=1)[CH2:21][N:19]([CH3:20])[C:18]([C:8]1[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[N:6][CH:7]=1)=[O:36]

Participants

6

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 10207712HCID 10207712, compound

Product 1

HCID 23502847HCID 23502847, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.50 g (0.98 mmol) 5-[(3,5-bis-trifluoromethyl-benzyl)-methyl-carbamoyl]-4-o-tolyl-pyridine-2-carboxylic acid methyl ester (Example 6), 10 ml methanol, 10 ml dioxane and 10 ml 1N aqueous sodium hydroxide solution was stirred at room temperature for 17 h. Dilution with water was followed by washing with tert-butyl methyl ether. The aqueous layer was acidified to pH 2 with 1 M aqueous hydrochloric acid solution and extracted with four portions of dichloromethane. The combined dichloromethane extracts were dried with sodium sulfate and concentrated to give 0.38 g (78%) of the title compound as a white solid.

Workup

  1. washby washing with tert-butyl methyl ether
  2. extractionextracted with four portions of dichloromethane
  3. dry with materialThe combined dichloromethane extracts were dried with sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e90826da4c824800957d1891a2fb8319
Source dataset
uspto-grants-2004_08
Patent number
US06770637B2

Reaction notes

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