p-Toluenesulfonic acid monohydrate → HCID 11037390, compound

HRID 1091299Notes

Reaction equation

HRID 1091299 reaction equation
[OH2:1].[C:2]1([CH3:12])[CH:7]=[CH:6][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1>C(O)C>[S:8]([O:11][CH2:7][C@H:2]([C@@H:3]([CH2:4][O:11][S:8]([C:5]1[CH:6]=[CH:7][C:2]([CH3:12])=[CH:3][CH:4]=1)(=[O:9])=[O:10])[OH:1])[OH:1])([C:5]1[CH:4]=[CH:3][C:2]([CH3:12])=[CH:7][CH:6]=1)(=[O:9])=[O:10]

Participants

3

Reactant 1

HCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 11037390HCID 11037390, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To an ethanol (100 mL) suspension of 1,4 di-O-tosyl-2,3-O-isopropylidene-L-threitol (10.0 g, 21.25 mmol), p-toluenesulfonic acid monohydrate (0.40 g) was added, and the mixture was heated to reflux for 4 days with stirring. The reaction liquor was cooled, and then the solvent was concentrated under reduced pressure. A saturated aqueous solution of sodium hydrogen carbonate (50 mL) was added to the obtained residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure, to obtain the title compound as a solid. This compound was used in the subsequent reaction without performing further purification.

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 4 days
  4. temperatureThe reaction liquor was cooled
  5. concentrationthe solvent was concentrated under reduced pressure
  6. additionA saturated aqueous solution of sodium hydrogen carbonate (50 mL) was added to the obtained residue
  7. extractionthe mixture was extracted with ethyl acetate
  8. washThe extract was washed with saturated brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5d08c030dd9e4d2787fb6e9517c13714
Source dataset
uspto-grants-2012_03
Patent number
US08129366B2

Reaction notes

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