Aspirin → HCID 22941431, compound

HRID 342710Notes

Reaction equation

HRID 342710 reaction equation
[C:1]([O:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=[O:8])(=[O:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].FC(F)(F)S(O[CH2:26][C@@H:27]1[CH2:31][O:30][C:29]2([CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]2)[O:28]1)(=O)=O>C(O)C.O.CN(C)C=O>[C:1]([O:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([O:9][CH2:26][C@@H:27]1[CH2:31][O:30][C:29]2([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]2)[O:28]1)=[O:8])(=[O:3])[CH3:2]

Participants

7

Reactant 3

HCID 2244AspirinHCID 10796Cesium carbonateHCID 22941432HCID 22941432, compound

Product 1

HCID 22941431HCID 22941431, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The solution from 2-acetoxy-benzoic acid (0.6 g, 3.33 mmol) in ethanol (3.5 ml) is treated with a solution of caesium carbonate (0.54 g, 1.67 mmol) in water (35 ml) and stirred. After 30 min, the mixture is freeze-dried. The residue is added with stirring to a solution of [2S]-1,4-dioxa-spiro[4,5]dec-2-yl-methyl trifluoromethanesulphonate (1.15 g, 3.79 mmol) in N,N-dimethylformamide (10 ml). After 16 h at 20° C., the mixture is concentrated, the residue is taken up in dichloromethane (50 ml), and the solution is washed twice with water, dried over magnesium sulphate and concentrated. The residue is purified by column chromatography (toluene/ethyl acetate=50/1). Yield: 601 mg.

Workup

  1. customthe mixture is freeze-dried
  2. additionThe residue is added
  3. waitAfter 16 h at 20° C.
  4. concentrationthe mixture is concentrated
  5. washthe solution is washed twice with water
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated
  8. customThe residue is purified by column chromatography (toluene/ethyl acetate=50/1)

Sources & evidence

ORD record
ord-cb1adae7a1264d6283b1963a180dd1b5
Source dataset
uspto-grants-1999_01
Patent number
US05859053

Reaction notes

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