Lithium Hydroxide → HCID 68816288, compound

HRID 732543Notes

Reaction equation

HRID 732543 reaction equation
C[O:2][C:3](=[O:26])[C:4]1[CH:16]=[C:15]([C:17]([F:25])([F:24])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:14]=[C:6]([C:7]([N:9]([CH3:13])[CH2:10][CH2:11][CH3:12])=[O:8])[CH:5]=1.[OH-].[Li+]>C1COCC1>[F:24][C:17]([F:25])([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:15]1[CH:14]=[C:6]([C:7]([N:9]([CH3:13])[CH2:10][CH2:11][CH3:12])=[O:8])[CH:5]=[C:4]([CH:16]=1)[C:3]([OH:26])=[O:2]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68814399HCID 68814399, compound

Product 1

HCID 68816288HCID 68816288, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Chill a solution of 5-(difluorophenyl-methyl)-N-methyl-N-propyl-isophthalamic acid methyl ester (0.043 g, 0.119 mmol) in THF (1 mL) in an ice bath. Add 1 N lithium hydroxide (0.18 mL, 0.18 mmol) and stir at room temperature for 3 h. Acidify the solution to about pH=2 and concentrate to one half of the solvent. Partition the residue between ethyl acetate and H2O. Extract the aqueous layer with ethyl acetate (2×10 mL). Wash the combined organic extract with saturated aqueous sodium chloride, dry (magnesium sulfate) and concentrate to give the title compound (95%).

Workup

  1. concentrationconcentrate to one half of the solvent
  2. customPartition the residue between ethyl acetate and H2O
  3. extractionExtract the aqueous layer with ethyl acetate (2×10 mL)
  4. washWash the combined
  5. extractionorganic extract with saturated aqueous sodium chloride
  6. dry with materialdry (magnesium sulfate)
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-4794d8e09566494fb3f43fed505b5958
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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