Hydrochloric Acid → HCID 20355557, compound

HRID 371654Notes

Reaction equation

HRID 371654 reaction equation
[CH2:1]([O:8][CH2:9][CH:10](O)[CH2:11][CH2:12][S:13]([NH2:16])(=[O:15])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+].Cl>N1C=CC=CC=1.CN(C)C=O.O>[CH2:1]([O:8][CH2:9][CH:10]1[CH2:11][CH2:12][S:13](=[O:15])(=[O:14])[NH:16]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 20355553HCID 20355553, compound

Product 1

HCID 20355557HCID 20355557, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-benzyloxy-3-hydroxy-1-butane-sulfonamide (1.6 g., 0.0062 mole) in pyridine (15 ml.), which is stirred and cooled in an ice bath, is added p-toluenesulfonyl chloride (1.18 g., 0.0062 mole). The reaction mixture is stirred at room temperature for 20 hours and then poured into water (100 ml.). This mixture is extracted with ethyl acetate-ether (1:1) (2 × 100 ml.). The organic phase is washed with brine, 3N hydrochloric acid, brine again, and then dried over sodium sulfate. Evaporation affords an oil that is dissolved in dimethylformamide (15 ml.); potassium carbonate (1.2 g.) is added, and the mixture is heated on the steam bath for 2.5 hours. Water is added to the cooled mixture, which is acidified (dilute HCl) and then extracted with ethyl acetate (2 × 75 ml.). The organic phase is washed with brine, dried over sodium sulfate, and concentrated in vacuo. The resulting oil is purified by chromatography over silica gel using ethyl acetate-hexane (60:40) to elute. From the proper fraction, there is obtained 1.2 g. (81%) of the title compound as a clear, viscous oil.

Workup

  1. temperaturecooled in an ice bath
  2. extractionThis mixture is extracted with ethyl acetate-ether (1:1) (2 × 100 ml.)
  3. washThe organic phase is washed with brine, 3N hydrochloric acid, brine again
  4. dry with materialdried over sodium sulfate
  5. customEvaporation
  6. customaffords an oil that
  7. temperaturethe mixture is heated on the steam bath for 2.5 hours
  8. extractionextracted with ethyl acetate (2 × 75 ml.)
  9. washThe organic phase is washed with brine
  10. dry with materialdried over sodium sulfate
  11. concentrationconcentrated in vacuo
  12. customThe resulting oil is purified by chromatography over silica gel
  13. washto elute
  14. customFrom the proper fraction, there is obtained 1.2 g

Sources & evidence

ORD record
ord-5e16724fc58347cca785c2921879ab16
Source dataset
uspto-grants-1978_05
Patent number
US04087435

Reaction notes

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