Diethyl Ether → trifluoro-methanesulfonic acid 2-morpholin-4-yl-4-oxo-4H-chromen-8-yl ester

HRID 1626717

반응식

HRID 1626717 반응식
O[C:2]1[C:7]([C:8](=[O:18])[CH2:9][C:10]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[O:11])=[CH:6][CH:5]=[CH:4][C:3]=1[O:19][S:20]([C:23]([F:26])([F:25])[F:24])(=[O:22])=[O:21].FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.CCOCC>ClCCl>[N:12]1([C:10]2[O:11][C:2]3[C:7]([C:8](=[O:18])[CH:9]=2)=[CH:6][CH:5]=[CH:4][C:3]=3[O:19][S:20]([C:23]([F:26])([F:24])[F:25])(=[O:21])=[O:22])[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1

참가 물질

5

반응물 3

HCID 3283Diethyl EtherHCID 67749Trifluoromethanesulfonic anhydrideHCID 11610960Trifluoro-methanesulfonic acid 2-hydroxy-3-(3-morpholin-4-yl-3-oxo-propionyl)-phenyl ester

생성물 1

HCID 11603298trifluoro-methanesulfonic acid 2-morpholin-4-yl-4-oxo-4H-chromen-8-yl ester

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Trifluoro-methanesulfonic acid 2-hydroxy-3-(3-morpholin-4-yl-3-oxo-propionyl)-phenyl ester [D] (1.06 g, 2.7 mmol) in dichloromethane (30 ml) was treated with trifluoromethanesulphonic anhydride and stirred over night at room temperature. The reaction mixture was then concentrated, re-dissolved in methanol and stirred for a further 2 hours. The solution was diluted with water and basified to pH8. It was then extracted three times with dichloromethane. The extracts were combined, washed with brine, dried with magnesium sulphate and evaporated to give the crude product as a brown oil. Trituration with ether gave trifluoro-methanesulfonic acid 2-morpholin-4-yl-4-oxo-4H-chromen-8-yl ester [E] as a brown solid. Yield 210 mg, 20%.

후처리

  1. concentrationThe reaction mixture was then concentrated
  2. dissolutionre-dissolved in methanol
  3. stirringstirred for a further 2 hours
  4. additionThe solution was diluted with water and basified to pH8
  5. extractionIt was then extracted three times with dichloromethane
  6. washwashed with brine
  7. dry with materialdried with magnesium sulphate
  8. customevaporated
  9. customto give the crude product as a brown oil

출처 및 근거

ORD 기록
ord-69c6190df50d495ab6df064ab3ab381b
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785457B2

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