p-Toluenesulfonic acid → HCID 131710046, compound

HRID 1283691Notes

Reaction equation

HRID 1283691 reaction equation
[CH2:1]([C:8]1[CH2:9][S:10][C@@H:11]2[CH:22]([NH:23]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[C:21](=[O:43])[N:12]2[C:13]=1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[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>CC(C)=O>[CH2:1]([C:8]1[CH2:9][S:10][C@@H:11]2[CH:22]([NH2:23])[C:21](=[O:43])[N:12]2[C:13]=1[C:14]([O:16][C:17]([CH3:20])([CH3:18])[CH3:19])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 68137441HCID 68137441, compound

Product 1

HCID 131710046HCID 131710046, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

t-Butyl 3-benzyl-7-triphenylmethylamino-3-cephem-4-carboxylate (929 mg) was dissolved in acetone (2 ml) and the solution cooled to -20°. p-Toluene sulphonic acid (330 mg) in acetone (2 ml) was added dropwise over 2 - 3 minutes and the solution left at 0° for 18 hours. The crystalline product was filtered, washed with a little cold acetone and dried (493 mg) m.p. 175°-177°. The mother liquors were taken up in ethyl acetate, washed with dilute aqueous sodium bicarbonate and brine, dried and evaporated. Chromatography on silica gave crystalline t-butyl 3-benzyl-7-amino-3-cephem-4-carboxylate (V). ##SPC11##

Workup

  1. temperaturethe solution cooled to -20°
  2. filtrationThe crystalline product was filtered
  3. washwashed with a little cold acetone
  4. customdried (493 mg) m.p. 175°-177°
  5. washwashed with dilute aqueous sodium bicarbonate and brine
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-b5e57e819ec341288b35a75c4cb82031
Source dataset
uspto-grants-1976_08
Patent number
US03975383

Reaction notes

Loading…