Hydrochloric Acid → 5-(2,2-Difluorovinyl)-N-methyl-N-propyl-isophthalamic acid

HRID 1436642Notes

Reaction equation

HRID 1436642 reaction equation
C([O:3][C:4](=[O:22])[C:5]1[CH:17]=[C:16]([CH:18]=[C:19]([F:21])[F:20])[CH:15]=[C:7]([C:8]([N:10]([CH3:14])[CH2:11][CH2:12][CH3:13])=[O:9])[CH:6]=1)C.[OH-].[Li+].Cl>C1COCC1>[F:20][C:19]([F:21])=[CH:18][C:16]1[CH:15]=[C:7]([C:8]([N:10]([CH3:14])[CH2:11][CH2:12][CH3:13])=[O:9])[CH:6]=[C:5]([CH:17]=1)[C:4]([OH:22])=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 688145195-(2,2-Difluorovinyl)-N-methyl-N-propyl-isophthalamic acid ethyl ester

Product 1

HCID 688140405-(2,2-Difluorovinyl)-N-methyl-N-propyl-isophthalamic acidYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Stir a solution of 5-(2,2-difluorovinyl)-N-methyl-N-propyl-isophthalamic acid ethyl ester (187 mg, 0.63 mmol), 1 N lithium hydroxide (2.5 mL, 2.5 mmol) and THF (2.5 mL) at room temperature overnight. Partition the reaction between ethyl acetate and water. Acidify the aqueous with 5 N HCl and extract with ethyl acetate. Dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with 2:98 to 6:94 methanol:dichloromethane with 1% acetic acid) to give the title compound (78 mg, 44%).

Workup

  1. customPartition
  2. customthe reaction between ethyl acetate and water
  3. extractionextract with ethyl acetate
  4. dry with materialDry (magnesium sulfate)
  5. concentrationconcentrate
  6. custompurify
  7. wash(silica gel chromatography, eluting with 2:98 to 6:94 methanol:dichloromethane with 1% acetic acid)

Sources & evidence

ORD record
ord-f52d462cb0b645ce8f9d4ddf6f3121f0
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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