Sodium Hydroxide → HCID 22025410, compound

HRID 733283Notes

Reaction equation

HRID 733283 reaction equation
C([O:3][C:4](=[O:24])[CH2:5][CH:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]([F:18])([F:17])[F:16])[CH:13]=2)[C:8](=[O:19])[N:7]1[CH2:20][CH:21]1[CH2:23][CH2:22]1)C.[OH-].[Na+]>C(O)C>[CH:21]1([CH2:20][N:7]2[C:8](=[O:19])[C:9]3[C:14](=[CH:13][C:12]([C:15]([F:17])([F:18])[F:16])=[CH:11][CH:10]=3)[CH:6]2[CH2:5][C:4]([OH:24])=[O:3])[CH2:23][CH2:22]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69058875HCID 69058875, compound

Product 1

HCID 22025410HCID 22025410, compoundYield 38.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.0 g of (2-cyclopropylmethyl-3-oxo-6-trifluoromethyl-2,3-dihydro-1H-isoindol-1-yl)acetic acid ethyl ester were dissolved using 10 ml of ethanol and 3.5 ml of a 1 N aqueous solution of NaOH added. The mixture was stirred for 3 h at ambient temperature and then the solvent removed in vacuo. Afterwards, 30 ml of water were added and the pH of the solution adjusted to pH=2 using aqueous HCl-solution. The solution was then extracted three times using 50 ml of EA each. The organic layer was dried over MgSO4 and the solvent was removed in vacuo to yield 0.35 g of an amorphous solid (Rf(EA/MeOH 5:1)=0.43; MS (ES+): 314 (M+1)+).

Workup

  1. additionadded
  2. customthe solvent removed in vacuo
  3. additionAfterwards, 30 ml of water were added
  4. extractionThe solution was then extracted three times
  5. dry with materialThe organic layer was dried over MgSO4
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-15302afcab74491683ad05ae71292cf1
Source dataset
uspto-grants-2009_09
Patent number
US07589117B2

Reaction notes

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