Thionyl Chloride → 6-Methoxy-2-(methoxycarbonylamino)indan-1-one

HRID 274090노트

반응식

HRID 274090 반응식
[CH3:1][O:2][C:3]([NH:5][C@H:6]([C:16]([OH:18])=O)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)=[O:4].S(Cl)(Cl)=O>ClCCl>[CH3:15][O:14][C:11]1[CH:10]=[C:9]2[C:8]([CH2:7][CH:6]([NH:5][C:3]([O:2][CH3:1])=[O:4])[C:16]2=[O:18])=[CH:13][CH:12]=1

참가 물질

4

반응물 2

HCID 24386Thionyl ChlorideHCID 54533786N-methoxycarbonyl-O-methyl-L-tyrosine

생성물 1

HCID 200947386-Methoxy-2-(methoxycarbonylamino)indan-1-one수율 25.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of N-methoxycarbonyl-O-methyl-L-tyrosine (0.5 g) in dichloromethane (2 ml) was added thionyl chloride (0.29 ml). After stirring for 1 hour at ambient temperature, the reaction mixture was concentrated in vacuo. The residue was dissolved in dichloromethane (5 ml) and treated with 0.9M ethylaluminum dichloride in dichloromethane (4.4 ml) in an ice-bath. The mixture was allowed to warm to ambient temperature and stirred overnight. The mixture was poured into concentrated hydrochloric acid containing crashed ice and extracted once with dichloromethane. The extract was washed with water and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. Purification of the residue by column chromatography on silica gel (eluent; 10:1 dichloromethane-ethyl acetate) gave 6-methoxy-2-(methoxycarbonylamino)indan-1-one (0.12 g).

후처리

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in dichloromethane (5 ml)
  3. additiontreated with 0.9M ethylaluminum dichloride in dichloromethane (4.4 ml) in an ice-bath
  4. temperatureto warm to ambient temperature
  5. stirringstirred overnight
  6. additionThe mixture was poured into concentrated hydrochloric acid containing
  7. extractionextracted once with dichloromethane
  8. washThe extract was washed with water and brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated in vacuo
  11. customPurification of the residue by column chromatography on silica gel (eluent; 10:1 dichloromethane-ethyl acetate)

출처 및 근거

ORD 기록
ord-d33e6921a9754b128e624ebe359f56df
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05387710

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