Trifluoroacetic anhydride → HCID 69004389, compound

HRID 230803Notes

Reaction equation

HRID 230803 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.CC1C=CC(S([N:24]=[C:25]2[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][N:26]2[CH:34]([CH3:44])[C:35](=O)[CH2:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])(=O)=O)=CC=1>ClCCl>[CH3:44][C:34]1[N:26]2[CH:27]=[C:28]([N+:31]([O-:33])=[O:32])[CH:29]=[CH:30][C:25]2=[N:24][C:35]=1[CH2:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39]

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 69002568HCID 69002568, compound

Product 1

HCID 69004389HCID 69004389, compoundYield 83.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

Trifluoroacetic anhydride (3 mL) was added to a dichloromethane solution (6 mL) of ethyl 5-[2-{[(4-methylphenyl)sulfonyl]imino}-5-nitropyridin-1(2H)-yl]-4-oxohexanoate (635 mg) obtained in Production Example 47-4, at room temperature. The reaction liquid was heated up to 40° C., stirred for 6 hours, and then concentrated under reduced pressure. Aqueous saturated sodium hydrogencarbonate solution was added to the residue, and extracted with ethyl acetate. The organic layer was dried with sodium sulfate, concentrated under reduced pressure, and the residue was purified through silica gel column chromatography (ethyl acetate/chloroform/hexane=1/1/1) to obtain the entitled compound (328 mg).

Workup

  1. customobtained in Production Example 47-4, at room temperature
  2. customThe reaction liquid
  3. concentrationconcentrated under reduced pressure
  4. additionAqueous saturated sodium hydrogencarbonate solution was added to the residue
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layer was dried with sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customthe residue was purified through silica gel column chromatography (ethyl acetate/chloroform/hexane=1/1/1)

Sources & evidence

ORD record
ord-6e78c1c7087a40a68b3a5e5757c30779
Source dataset
uspto-grants-2009_07
Patent number
US07566781B2

Reaction notes

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