Hydrochloric Acid → 5-(3,3-Difluoropyrrolidine-1-carbonyl)-N-methyl-N-propyl-isophthalamic acid

HRID 1436646Notes

Reaction equation

HRID 1436646 reaction equation
C([O:3][C:4](=[O:27])[C:5]1[CH:17]=[C:16]([C:18]([N:20]2[CH2:24][CH2:23][C:22]([F:26])([F:25])[CH2:21]2)=[O:19])[CH:15]=[C:7]([C:8]([N:10]([CH3:14])[CH2:11][CH2:12][CH3:13])=[O:9])[CH:6]=1)C.[OH-].[Li+].C1COCC1.Cl>O>[F:26][C:22]1([F:25])[CH2:23][CH2:24][N:20]([C:18]([C:16]2[CH:15]=[C:7]([C:8]([N:10]([CH3:14])[CH2:11][CH2:12][CH3:13])=[O:9])[CH:6]=[C:5]([CH:17]=2)[C:4]([OH:27])=[O:3])=[O:19])[CH2:21]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 688143585-(3,3-Difluoropyrrolidine-1-carbonyl)-N-methyl-N-propyl-isophthalamic acid ethyl ester

Product 1

HCID 688158735-(3,3-Difluoropyrrolidine-1-carbonyl)-N-methyl-N-propyl-isophthalamic acidYield 104.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Stir a solution of 5-(3,3-difluoropyrrolidine-1-carbonyl)-N-methyl-N-propyl-isophthalamic acid ethyl ester (270 mg, 0.71 mmol), 1 N lithium hydroxide (1.1 mL, 1.1 mmol) and THF (2.0 mL) at room temperature for 4 h. Add 10 mL water, acidify with 1 N HCl (2 mL), extract with dichloromethane (3×10 mL), dry (sodium sulfate) and concentrate to give the title compound (262 mg, 100%).

Workup

  1. extractionextract with dichloromethane (3×10 mL)
  2. dry with materialdry (sodium sulfate)
  3. concentrationconcentrate

Sources & evidence

ORD record
ord-826c05cf75b042d28617363e627da9fa
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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