Trifluoroacetic acid → (+/-)-Cyclopentyl{4-[(5,6-difluoro-1-oxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}acetic acid

HRID 877241Notes

Reaction equation

HRID 877241 reaction equation
[CH:1]1([CH:6]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][N:21]3[CH2:29][C:28]4[C:23](=[CH:24][C:25]([F:31])=[C:26]([F:30])[CH:27]=4)[C:22]3=[O:32])=[CH:16][CH:15]=2)[C:7]([O:9]C(C)(C)C)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O>ClCCl>[CH:1]1([CH:6]([C:14]2[CH:15]=[CH:16][C:17]([CH2:20][N:21]3[CH2:29][C:28]4[C:23](=[CH:24][C:25]([F:31])=[C:26]([F:30])[CH:27]=4)[C:22]3=[O:32])=[CH:18][CH:19]=2)[C:7]([OH:9])=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58136606tert-butyl(+/-)-cyclopentyl{4-[(5,6-difluoro-1-oxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}acetate

Product 1

HCID 58136486(+/-)-Cyclopentyl{4-[(5,6-difluoro-1-oxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}acetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

27.0 mg (0.06 mmol) of tert-butyl(+/−)-cyclopentyl{4-[(5,6-difluoro-1-oxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}acetate were initially charged in 200 μl of dichloromethane, and 94 μl of trifluoroacetic acid were added. The mixture was stirred at RT for 2 h. The reaction mixture was then concentrated on a rotary evaporator, and the residue was dried under high vacuum. This gave 23.5 mg (99.7% of theory) of the target compound.

Workup

  1. concentrationThe reaction mixture was then concentrated on a rotary evaporator
  2. customthe residue was dried under high vacuum

Sources & evidence

ORD record
ord-4337e93bf8af43e78129dd8a56cd85e9
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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