Trifluoromethanesulfonic acid → HCID 67157467, compound

HRID 1868182Notes

Reaction equation

HRID 1868182 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][F: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]([O:15][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[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][F:27])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 62406Trifluoromethanesulfonic acidHCID 144968Benzyl 2,2,2-trichloroacetimidateHCID 516892Sodium BicarbonateHCID 67157509HCID 67157509, compound

Product 1

HCID 67157467HCID 67157467, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21916607Dichloromethane cyclohexaneSolvent

Procedure

The compound (344 mg, 0.92 mmol) synthesized in Example 10 (10a) was dissolved in methylene chloride:cyclohexane (1:2, 10 mL) and benzyl trichloroacetoimidate (0.68 mL, 3.68 mmol) and trifluoromethane sulfonic acid (16 μL, 0.18 mmol) were added thereto, followed by stirring of the mixture at room temperature for 4 hours. After saturated aqueous sodium hydrogencarbonate (1 mL) was added to the reaction mixture at 0° C. and the mixture was diluted with ethyl acetate (20 mL), the mixture was washed with water (20 mL) and saturated brine (20 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, 8:1-5:1, V/V) to obtain a colorless oil (307 mg, 68%).

Workup

  1. washthe mixture was washed with water (20 mL) and saturated brine (20 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-85ee4d72ebf947ec9ba62ecfdc0948d0
Source dataset
uspto-grants-2009_12
Patent number
US07632930B2

Reaction notes

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