Water → (+/-)-2-Cyclopentyl-2-(4-((1,3-dioxoisoindolin-2-yl)methyl)phenyl)acetic acid

HRID 877224Notes

Reaction equation

HRID 877224 reaction equation
[CH:1]1([CH:6]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][N:21]3[C:29](=[O:30])[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[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.O>ClCCl>[CH:1]1([CH:6]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][N:21]3[C:22](=[O:31])[C:23]4[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=4)[C:29]3=[O:30])=[CH:16][CH:15]=2)[C:7]([OH:9])=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 58136372tert-Butyl cyclopentyl{4-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}acetate

Product 1

HCID 58136304(+/-)-2-Cyclopentyl-2-(4-((1,3-dioxoisoindolin-2-yl)methyl)phenyl)acetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

8.5 g (20.26 mmol) of tert-butyl(+/−)-2-cyclopentyl-2-(4-((1,3-dioxoisoindolin-2-yl)methyl)-phenyl)acetate were initially charged in 95 ml of dichloromethane, 31.2 ml (405.2 mmol) of trifluoroacetic acid were added and the mixture was stirred at room temperature for 2 h. Water (250 ml) was then added, and the reaction mixture was extracted with dichloromethane. The organic phase was washed with water, dried over magnesium sulfate and concentrated. This gave 6.98 g (95% of theory) of the target compound.

Workup

  1. extractionthe reaction mixture was extracted with dichloromethane
  2. washThe organic phase was washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-18a08a81714c4e22bf92d89bfb3302e1
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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