Hydrochloric Acid → 4,4,4-Trifluoro-3-methyl-2-{4-[(1-oxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}butanoic acid

HRID 877239Notes

Reaction equation

HRID 877239 reaction equation
[F:1][C:2]([F:29])([F:28])[CH:3]([CH3:27])[CH:4]([C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:17]2[CH2:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]2=[O:26])=[CH:12][CH:11]=1)[C:5]([O:7]CC)=[O:6].CO.[OH-].[Li+].Cl>C1COCC1.O>[F:29][C:2]([F:1])([F:28])[CH:3]([CH3:27])[CH:4]([C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:17]2[CH2:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]2=[O:26])=[CH:12][CH:11]=1)[C:5]([OH:7])=[O:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 58136395ethyl 4,4,4-trifluoro-3-methyl-2-{4-[(1-oxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}butanoate

Product 1

HCID 581366264,4,4-Trifluoro-3-methyl-2-{4-[(1-oxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}butanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Under argon, 270 mg (0.66 mmol) of ethyl 4,4,4-trifluoro-3-methyl-2-{4-[(1-oxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}butanoate were dissolved in 1 ml each of THF, methanol and water, and 69.9 mg (1.66 mmol) of lithium hydroxide were added. The mixture was stirred at RT overnight. The reaction mixture was diluted with water and acidified with 1 N hydrochloric acid, and the resulting precipitate was filtered off with suction. The solid was washed with water until the washings remained neutral. This gave 222 mg (88.3% of theory) of the target compound.

Workup

  1. filtrationthe resulting precipitate was filtered off with suction
  2. washThe solid was washed with water until the washings

Sources & evidence

ORD record
ord-7509ab0e2426400c9ef107b4a15f6fed
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

Loading…