p-Toluenesulfonic acid → HCID 13922881, compound

HRID 2232361Notes

Reaction equation

HRID 2232361 reaction equation
[CH3:1][C:2]1([C:7]2[CH:8]=[CH:9][C:10]3[CH:14]=[C:13]([S:15](=[O:18])(=[O:17])[NH2:16])[S:12][C:11]=3[CH:19]=2)OCC[O:3]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[C:2]([C:7]1[CH:8]=[CH:9][C:10]2[CH:14]=[C:13]([S:15](=[O:18])(=[O:17])[NH2:16])[S:12][C:11]=2[CH:19]=1)(=[O:3])[CH3:1]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 13922880HCID 13922880, compound

Product 1

HCID 13922881HCID 13922881, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The ketal product from Example 37 (4.4 g, 14.7 mmole) and p-toluenesulfonic acid (400 mg) were dissolved in acetone (90 ml). The mixture was stirred overnight. The solvent was removed in vacuo and the residue partitioned between ethyl acetate (200 ml) and 10% saturated NaHCO3 solution (b 100 ml). The organic layer was washed with H2O (2×100 ml) and dried over Na2SO4. The solvent was removed in vacuo and the residue was triturated with hot CHCl3 (100 ml). Upon cooling, 3.4 g (90.6%) of product was obtained, m.p. 154°-155° C.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue partitioned between ethyl acetate (200 ml) and 10% saturated NaHCO3 solution (b 100 ml)
  3. washThe organic layer was washed with H2O (2×100 ml)
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed in vacuo
  6. customthe residue was triturated with hot CHCl3 (100 ml)
  7. temperatureUpon cooling

Sources & evidence

ORD record
ord-e1f1664c892841d8b3a233a1729506cf
Source dataset
uspto-grants-1988_11
Patent number
US04788192

Reaction notes

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