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

HRID 1751100

反応式

HRID 1751100 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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);

後処理

  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

出典と根拠

ORDレコード
ord-56aedeab4e41445cabcf3cd9901bb1a6
出典データセット
uspto-grants-2015_10
特許番号
US09156840B2

関連ノート

読み込み中…