Trifluoromethanesulfonic acid → HCID 67157834, compound

HRID 901789Notes

Reaction equation

HRID 901789 reaction equation
[C:1]([O:9][C@H:10]1[C@H:14]([OH:15])[CH2:13][N:12]([C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[C@@H:11]1[CH2:26][OH:27])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC(Cl)(Cl)C(=N)O[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.FC(F)(F)S(O)(=O)=O.C(=O)([O-])O.[Na+]>C(Cl)Cl.C1CCCCC1.C(OCC)(=O)C>[C:1]([O:9][C@H:10]1[C@H:14]([OH:15])[CH2:13][N:12]([C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[C@@H:11]1[CH2:26][O:27][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 62406Trifluoromethanesulfonic acidHCID 144968Benzyl 2,2,2-trichloroacetimidateHCID 516892Sodium BicarbonateHCID 67157096HCID 67157096, compound

Product 1

HCID 67157834HCID 67157834, compoundYield 112.5%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21916607Dichloromethane cyclohexaneSolvent

Procedure

The compound (3.37 g, 9.07 mmol) synthesized in Example 1 (1h) was dissolved in methylene chloride:cyclohexane (1:2, 180 mL) and benzyl trichloroacetoimidate (2.0 mL, 10.88 mmol) and trifluoromethanesulfonic acid (2.57 mL, 15.3 mmol) were added thereto, followed by stirring of the mixture at room temperature for 1 hour. After saturated aqueous sodium hydrogencarbonate solution (20 mL) was added to the reaction mixture at 0° C. and the mixture was diluted with ethyl acetate (200 mL), it was washed with water (300 mL) and saturated aqueous sodium hydrogencarbonate solution (300 mL) and dried with anhydrous sodium sulfate, followed by distilling off of the solvent under reduced pressure. The residue was purified using silica gel flash column chromatography (hexane:ethyl acetate, 5:1-2:1, V/V) to obtain 4.71 g of pale yellow oil.

Workup

  1. washwas washed with water (300 mL) and saturated aqueous sodium hydrogencarbonate solution (300 mL)
  2. dry with materialdried with anhydrous sodium sulfate
  3. distillationby distilling off of the solvent under reduced pressure
  4. customThe residue was purified

Sources & evidence

ORD record
ord-51cb822a21be45a88d33dc5d4d24f028
Source dataset
uspto-grants-2008_04
Patent number
US07361744B2

Reaction notes

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