Trifluoroacetic acid → cyclopentyl{4-[(4-fluoro-1-oxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}acetic acid

HRID 877246Notes

Reaction equation

HRID 877246 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][CH:25]=[CH:26][C:27]=4[F:30])[C:22]3=[O:31])=[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:19]=[CH:18][C:17]([CH2:20][N:21]3[CH2:29][C:28]4[C:23](=[CH:24][CH:25]=[CH:26][C:27]=4[F:30])[C:22]3=[O:31])=[CH:16][CH:15]=2)[C:7]([OH:9])=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58136532tert-Butyl(+/-)-cyclopentyl{4-[(4-fluoro-1-oxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-phenyl}acetate

Product 1

HCID 58136462cyclopentyl{4-[(4-fluoro-1-oxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}acetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

150.0 mg (0.35 mmol) of tert-butyl(+/−)-cyclopentyl{4-[(4-fluoro-1-oxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}acetate were initially charged in 300 μl of dichloromethane, and 515 μl of trifluoroacetic acid were added. The mixture was stirred at RT for 1 h. The reaction mixture was then concentrated on a rotary evaporator, and the residue was dried under high vacuum. Acetonitrile was added to the product, and the precipitated solid was triturated and then filtered off with suction. This gave 112.0 mg (86.1% 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
  3. additionAcetonitrile was added to the product
  4. customthe precipitated solid was triturated
  5. filtrationfiltered off with suction

Sources & evidence

ORD record
ord-4affdd6c165647f4abdcae21663de8c7
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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