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

HRID 571278노트

반응식

HRID 571278 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-8fb56a23a70c47178497a89eee1d70ef
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09024027B2

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