p-Toluenesulfonic acid → HCID 131710049, compound

HRID 1283692Notes

Reaction equation

HRID 1283692 reaction equation
[F:1][C:2]1[CH:44]=[CH:43][C:5]([CH2:6][C:7]2[CH2:8][S:9][C@@H:10]3[CH:21]([NH:22]C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[C:20](=[O:42])[N:11]3[C:12]=2[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[NH2:22][CH:21]1[C:20](=[O:42])[N:11]2[C:12]([C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])=[C:7]([CH2:6][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:44][CH:43]=3)[CH2:8][S:9][C@H:10]12

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acid2×HCID 131710048HCID 131710048, compound2×

Product 1

HCID 131710049HCID 131710049, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent3×

Procedure

t-Butyl 3-p-fluorobenzyl-7-triphenylmethylamino-3-cephem-4-carboxylate (IX) (72 mg) was dissolved in acetone and the solution cooled to 0°. p-Toluene sulphonic acid (25 mg) in acetone (0.5 ml) was added dropwise over a few minutes and the solution left to warm to room temperature with stirring. After 2.5 hours a solid had formed but t.l.c. still showed some unchanged (IX) to be present. The mixture was again cooled to 0° and a further quantity of p-toluene sulphonic acid (5 mg) in acetone added. After leaving at room temperature for a further 1.5 hours, the white solid was filtered off. This solid was suspended in ethyl acetate and treated with saturated sodium bicarbonate solution. The organic layer was washed with brine, dried and evaporated to give t-butyl 7-amino-3-p-fluorobenzyl-3-cephem-4-carboxylate (XI) (28 mg) shown to be pure by t.l.c. ##SPC17##

Workup

  1. temperaturethe solution cooled to 0°
  2. waitthe solution left
  3. customAfter 2.5 hours a solid had formed
  4. temperatureThe mixture was again cooled to 0°
  5. customAfter leaving at room temperature for a further 1.5 hours
  6. filtrationthe white solid was filtered off
  7. additiontreated with saturated sodium bicarbonate solution
  8. washThe organic layer was washed with brine
  9. customdried
  10. customevaporated

Sources & evidence

ORD record
ord-db2f173d6d3d4558ad6282e87ff7ee9c
Source dataset
uspto-grants-1976_08
Patent number
US03975383

Reaction notes

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