Trifluoromethanesulfonic acid → HCID 14743303, compound

HRID 1368701Notes

Reaction equation

HRID 1368701 reaction equation
[C:1]([O:6][CH2:7][CH3:8])(=[O:5])[C@H:2]([CH3:4])[OH:3].ClC(Cl)(Cl)C(=N)O[CH2:13][CH:14]=[CH2:15].FC(F)(F)S(O)(=O)=O>C1CCCCC1>[CH2:15]([O:3][C@@H:2]([CH3:4])[C:1]([O:6][CH2:7][CH3:8])=[O:5])[CH:14]=[CH2:13]

Participants

5

Reactant 3

HCID 62406Trifluoromethanesulfonic acidHCID 92831(L)-ethyl lactateHCID 316905Allyl 2,2,2-Trichloroacetimidate

Product 1

HCID 14743303HCID 14743303, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent2×

Procedure

7.08 g (60 mmol) of ethyl (S)-(−)-lactate are introduced into 120 ml of cyclohexane, and 25.0 g (120 mmol) of allyl trichloroacetimidate, dissolved in 30 ml of cyclohexane, are added thereto. 0.55 ml (6 mmol) of trifluoromethanesulfonic acid are then added and the mixture is stirred for 16 h. When the reaction is complete, the precipitated trichloroacetamide is filtered off with suction and washed with cyclohexane. The filtrate is washed with saturated NaHCO3 solution, after which the organic phase is dried over Na2SO4, filtered and evaporated on a rotary evaporator. Flash-chromatographic purification (cyclohexane/EtOAc=10:1; Rf=0.27) gives 6.9 g (72%) of a colorless liquid.

Workup

  1. additionare added
  2. filtrationthe precipitated trichloroacetamide is filtered off with suction
  3. washwashed with cyclohexane
  4. washThe filtrate is washed with saturated NaHCO3 solution
  5. dry with materialafter which the organic phase is dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated on a rotary evaporator
  8. customFlash-chromatographic purification (cyclohexane/EtOAc=10:1; Rf=0.27)

Sources & evidence

ORD record
ord-32c1191792dc43e4bc376298321084f5
Source dataset
uspto-grants-2003_06
Patent number
US06573391B1

Reaction notes

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