p-Toluenesulfonic acid → HCID 131710043, compound

HRID 1283689Notes

Reaction equation

HRID 1283689 reaction equation
[CH2:1]([C:8]1[CH2:9][S:10][C@@H:11]2[CH:19]([NH:20]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[C:18](=[O:40])[N:12]2[C:13]=1[C:14]([O:16][CH3:17])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)(=O)C>CC(C)=O>[CH2:1]([C:8]1[CH2:9][S:10][C@@H:11]2[CH:19]([NH2:20])[C:18](=[O:40])[N:12]2[C:13]=1[C:14]([O:16][CH3:17])=[O:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acid2×HCID 8857Ethyl AcetateHCID 131710044HCID 131710044, compound

Product 1

HCID 131710043HCID 131710043, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

Methyl 3-benzyl-7-tritylamino-3-cephem-4-carboxylate (111 mg) was dissolved in acetone (1.5 ml.) and the solution cooled to -20°. p-Toluene sulphonic acid (40 mg) in acetone (0.5 ml) was added dropwise over a few minutes and the solution left at 0° for 16 hours. Thin layer chromatography (TLC) still showed some unchanged starting material was present. A further quantity of p-toluene sulphonic acid (10 mg) was added and the solution left at room temperature for 4 hours. Ethyl acetate was added and the solution washed with dilute aqueous sodium bicarbonate and brine. Evaporation of the dried organic layer afforded methyl 3-benzyl-7-amino-3-cephem-4-carboxylate contaminated with trityl alcohol.

Workup

  1. temperaturethe solution cooled to -20°
  2. waitthe solution left at room temperature for 4 hours
  3. washthe solution washed with dilute aqueous sodium bicarbonate and brine
  4. customEvaporation of the dried organic layer

Sources & evidence

ORD record
ord-93014120d9844b03b2ede35e447979b8
Source dataset
uspto-grants-1976_08
Patent number
US03975383

Reaction notes

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