Trifluoromethanesulfonic acid → HCID 11423781, compound

HRID 2275821Notes

Reaction equation

HRID 2275821 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:11][CH2:10][C:9]2=[O:12])=[CH:4][CH:3]=1.FC(F)(F)S(O)(=O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[F:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[NH:8][CH2:11][CH2:10][C:9]2=[O:12]

Participants

5

Reactant 3

HCID 62406Trifluoromethanesulfonic acid2×HCID 516892Sodium BicarbonateHCID 11412579HCID 11412579, compound

Product 1

HCID 11423781HCID 11423781, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

500 mg of 1-(4-fluorophenyl)azetidin-2-one (Example 154A, 3.03 mmol, 1 equivalent) were initially charged in 24 ml of dichloromethane, 0.5 ml of trifluoromethanesulphonic acid (909 mg, 6.05 mmol, 2 equivalents) were added at 0° C. and the mixture was stirred at RT for 45 min. Two more times, 0.3 equivalents of trifluoromethanesulphonic acid were added, and after each addition the mixture was stirred for 30 min. With ice cooling, saturated aqueous sodium bicarbonate solution was added carefully, and the reaction mixture was extracted three times with dichloromethane. The combined organic phases were dried over sodium sulphate, filtered and concentrated. This gave 284 mg (57% of theory) of the title compound.

Workup

  1. additionafter each addition the mixture
  2. stirringwas stirred for 30 min
  3. extractionthe reaction mixture was extracted three times with dichloromethane
  4. dry with materialThe combined organic phases were dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d08b573698be4e5abfa16021e2f5ffce
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Reaction notes

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