Sodium Hydroxide → Tert-butyl 2-(4-(methylsulfonamido)-1,3-dioxoisoindolin-2-yl)acetate

HRID 571279Notes

Reaction equation

HRID 571279 reaction equation
[CH3:1][S:2]([N:5]([C:10]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:11]=1[C:12](=[O:28])[N:13]([CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:14]2=[O:19])S(C)(=O)=O)(=[O:4])=[O:3].[OH-].[Na+]>CC#N>[CH3:1][S:2]([NH:5][C:10]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:11]=1[C:12](=[O:28])[N:13]([CH2:20][C:21]([O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:22])[C:14]2=[O:19])(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 89511917tert-butyl 2-(4-(N-(methylsulfonyl)methylsulfonamido)-1,3-dioxoisoindolin-2-yl)acetate

Product 1

HCID 86681686Tert-butyl 2-(4-(methylsulfonamido)-1,3-dioxoisoindolin-2-yl)acetateYield 43.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of tert-butyl 2-(4-(N-(methylsulfonyl)methylsulfonamido)-1,3-dioxoisoindolin-2-yl)acetate (548 mg, 1.267 mmol) in MeCN (5 ml), aqueous 2N NaOH (1457 μl, 2.91 mmol) was added, and the mixture was stirred at room temperature for 24 hours. The solvent was evaporated and the residue was diluted with water, acidified and extracted twice with ethyl acetate; the organic phase was washed with brine, dried over sodium sulfate and evaporated. The residue was purified by flash chromatography on silica gel (EtOAc/hexane 8/2) to obtain tert-butyl 2-(4-(methylsulfonamido)-1,3-dioxoisoindolin-2-yl)acetate as an off-white solid (196 mg, 0.553 mmol, 43.6% yield, MS/ESI+ 376.8 [MNa]+).

Workup

  1. customThe solvent was evaporated
  2. additionthe residue was diluted with water
  3. extractionextracted twice with ethyl acetate
  4. washthe organic phase was washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customThe residue was purified by flash chromatography on silica gel (EtOAc/hexane 8/2)

Sources & evidence

ORD record
ord-108e531ed76646a8bc5db7c958bf0e77
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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