Triethylamine → tert-butyl 2-(4-(N-(methylsulfonyl)methylsulfonamido)-1,3-dioxoisoindolin-2-yl)acetate

HRID 571278Notes

Reaction equation

HRID 571278 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:20])[N:5]([CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:6]2=[O:11].C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>C(Cl)Cl>[CH3:28][S:29]([N:1]([C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:20])[N:5]([CH2:12][C:13]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:14])[C:6]2=[O:11])[S:29]([CH3:28])(=[O:31])=[O:30])(=[O:31])=[O:30]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86681685Tert-butyl 2-(4-amino-1,3-dioxoisoindolin-2-yl)acetate

Product 1

HCID 89511917tert-butyl 2-(4-(N-(methylsulfonyl)methylsulfonamido)-1,3-dioxoisoindolin-2-yl)acetateYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl 2-(4-amino-1,3-dioxoisoindolin-2-yl)acetate (712 mg, 2.58 mmol), triethylamine (1029 μl, 7.73 mmol) and methanesulfonyl chloride (602 μl, 7.73 mmol) in 20 ml of DCM was stirred overnight at room temperature. The mixture was washed with 1N HCl, brine and finally dried over sodium sulfate and evaporated; the residue was purified by flash chromatography (Hexane/EtOAc 3/1 to 1/1) yielding tert-butyl 2-(4-(N-(methylsulfonyl)methylsulfonamido)-1,3-dioxoisoindolin-2-yl)acetate as an off-white foam (0.96 g, 2.220 mmol, 86% yield, MS/ESI+ 454.8 [MNa]+) and used in the following reaction without further purification.

Workup

  1. washThe mixture was washed with 1N HCl, brine
  2. dry with materialfinally dried over sodium sulfate
  3. customevaporated
  4. customthe residue was purified by flash chromatography (Hexane/EtOAc 3/1 to 1/1)

Sources & evidence

ORD record
ord-8fb56a23a70c47178497a89eee1d70ef
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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