Acetic Acid → Methyl 3-(2-oxoindolin-3-yl)propanoate

HRID 1751100

반응식

HRID 1751100 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:2]1.C(O)(=[O:18])C.CS(C)=O.Cl>O>[O:18]=[C:2]1[CH:3]([CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1]1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 21711Methyl 3-(1H-indol-3-yl)propanoate

생성물 1

HCID 14903583Methyl 3-(2-oxoindolin-3-yl)propanoate수율 98%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of methyl 3-indolepropionate (5.00 g, 0.0246 mol), acetic acid (10 mL), dimethylsulfoxide (26 mL, 0.369 mol, 15 eq.) and concentrated hydrogen chloride (37%) (22 mL, 0.738 mol, 30 eq.) was stirred at ambient temperature for 2.5 h. Water was added to the mixture and the mixture was extracted with ethyl acetate. The organic layer was dried over MgSO4, filtered and concentrated in vacuo. The crude residue was purified using the Biotage flash chromatography system (30% ethyl acetate in hexanes) to afford the title compound as an oil (5.28 g, 98%); 1H NMR (DMSO-d6); 62.03-2.10 (m, 2H); 2.32-2.39 (m, 2H); 3.46 (t, J=6.4 Hz, 1H); 3.54 (s, 3H); 6.81 (d, J=7.6 Hz, 1H); 6.93-6.97 (m, 1H); 7.15-7.17 (m, 1H); 7.24 (d, J=7.6 Hz, 1H);

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified

출처 및 근거

ORD 기록
ord-56aedeab4e41445cabcf3cd9901bb1a6
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156840B2

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