Trifluoroacetic acid → (+)-Cyclopentyl{4-[(1-oxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}ethanoic Acid

HRID 238184Notes

Reaction equation

HRID 238184 reaction equation
FC(F)(F)C(O)=O.[CH:8]1([CH:13]([C:21]2[CH:26]=[CH:25][C:24]([CH2:27][N:28]3[CH2:36][C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[C:29]3=[O:37])=[CH:23][CH:22]=2)[C:14]([O:16]C(C)(C)C)=[O:15])[CH2:12][CH2:11][CH2:10][CH2:9]1>ClCCl>[CH:8]1([CH:13]([C:21]2[CH:26]=[CH:25][C:24]([CH2:27][N:28]3[CH2:36][C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[C:29]3=[O:37])=[CH:23][CH:22]=2)[C:14]([OH:16])=[O:15])[CH2:9][CH2:10][CH2:11][CH2:12]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58074501tert-butyl(+)-cyclopentyl{4-[(1-oxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}-ethanoate

Product 1

HCID 58074558(+)-Cyclopentyl{4-[(1-oxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}ethanoic Acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

640 μl (7.4 mmol) of trifluoroacetic acid were added dropwise to a solution of 300 mg (0.740 mmol) of tert-butyl(+)-cyclopentyl{4-[(1-oxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}-ethanoate in 1.5 ml dichloromethane. After 1 h of stirring, the reaction mixture was concentrated under reduced pressure and the residue was dried under high vacuum. This gave 267 mg (100% of theory) of the title compound.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customthe residue was dried under high vacuum

Sources & evidence

ORD record
ord-8f77a4dc30e148eca8c5130677038796
Source dataset
uspto-grants-2014_02
Patent number
US08642592B2

Reaction notes

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