Water → HCID 67170535, compound

HRID 1918355Notes

Reaction equation

HRID 1918355 reaction equation
C[O:2][C:3]([C:5]1([NH:12][C:13](=[O:36])[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][C:23]3[CH:24]=[C:25]([CH3:29])[CH:26]=[CH:27][CH:28]=3)=[C:16]([CH:30]([OH:35])[C:31]([F:34])([F:33])[F:32])[CH:15]=2)[CH2:10][CH2:9][CH:8]([CH3:11])[CH2:7][CH2:6]1)=[O:4].[OH-].[Li+].O>CO>[CH3:11][CH:8]1[CH2:7][CH2:6][C:5]([NH:12][C:13](=[O:36])[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][C:23]3[CH:24]=[C:25]([CH3:29])[CH:26]=[CH:27][CH:28]=3)=[C:16]([CH:30]([OH:35])[C:31]([F:32])([F:33])[F:34])[CH:15]=2)([C:3]([OH:4])=[O:2])[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 962Water2×HCID 3939Lithium HydroxideHCID 67169661HCID 67169661, compound

Product 1

HCID 67170535HCID 67170535, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

170 mg of 4-Methyl-1-[4-(2-m-tolyl-ethoxy)-3-(2,2,2-trifluoro-1-hydroxy-ethyl)-benzoylamino]-cyclohexanecarboxylic acid methyl ester and 28 mg of lithium hydroxide were stirred in 50 ml of methanol and 1 ml of water for 5 h at 40° C. The reaction mixture was then diluted using 10 ml of water, the methanol evaporated and acidified to pH=2 using aqueous NaHSO4-solution. The mixture was then stirred for 30 minutes at room temperature, the product isolated by filtration and dried in vacuo to yield 138 mg of the title compound.

Workup

  1. additionThe reaction mixture was then diluted
  2. customthe methanol evaporated
  3. customthe product isolated by filtration
  4. customdried in vacuo

Sources & evidence

ORD record
ord-ccd3d04248e44952bf0e7182c9e6528b
Source dataset
uspto-grants-2013_12
Patent number
US08618304B2

Reaction notes

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