Methanol → HCID 67169908, compound

HRID 1918360Notes

Reaction equation

HRID 1918360 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([Cl:26])[CH:19]=2)[C:8]([O:11][CH:12]2[CH2:15][C:14]([F:17])([F:16])[CH2:13]2)=[CH:9][CH:10]=1)=[O:4].[Li+].[OH-].CO>O>[Cl:26][C:20]1[CH:19]=[C:18]([C:7]2[C:8]([O:11][CH:12]3[CH2:13][C:14]([F:17])([F:16])[CH2:15]3)=[CH:9][CH:10]=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=2)[CH:23]=[CH:22][C:21]=1[O:24][CH3:25]

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium Hydroxide2×HCID 67170195HCID 67170195, compound

Product 1

HCID 67169908HCID 67169908, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

85 mg of 3′-Chloro-6-(3,3-difluoro-cyclobutoxy)-4′-methoxy-biphenyl-3-carboxylic acid methyl ester and 14 mg of LiOH (monohydrate) were dissolved using 5 ml of methanol and 0.5 ml of water. The mixture was stirred for 15 h at room temperature. Then, 14 mg of LiOH (monohydrate) were added and the reaction mixture stirred for 24 h at room temperature. Then, 10 ml of water were added and the methanol evaporated. The mixture was then acidified to pH=2 using aqueous NaHSO4-solution. The mixture was stirred for 30 minutes at room temperature. The product was then collected by filtration and dried in vacuo to yield 65 mg of the title compound that was used without further purification.

Workup

  1. stirringthe reaction mixture stirred for 24 h at room temperature
  2. customthe methanol evaporated
  3. stirringThe mixture was stirred for 30 minutes at room temperature
  4. filtrationThe product was then collected by filtration
  5. customdried in vacuo

Sources & evidence

ORD record
ord-ea22da8e82ab46028cf6be8f26412197
Source dataset
uspto-grants-2013_12
Patent number
US08618304B2

Reaction notes

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