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

HRID 1626717Notes

Reaction equation

HRID 1626717 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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%.

Workup

  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

Sources & evidence

ORD record
ord-69c6190df50d495ab6df064ab3ab381b
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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