p-Toluenesulfonic acid monohydrate → HCID 131710039, compound

HRID 1578879Notes

Reaction equation

HRID 1578879 reaction equation
[C:1]1([CH2:7][CH2:8][C:9]2[CH2:10][S:11][C@@H:12]3[CH:23]([NH:24]C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[C:22](=[O:44])[N:13]3[C:14]=2[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[C:1]1([CH2:7][CH2:8][C:9]2[CH2:10][S:11][C@@H:12]3[CH:23]([NH2:24])[C:22](=[O:44])[N:13]3[C:14]=2[C:15]([O:17][C:18]([CH3:20])([CH3:21])[CH3:19])=[O:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 131710040HCID 131710040, compound

Product 1

HCID 131710039HCID 131710039, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The cephem (XX111) (77 mg) was dissolved in acetone (1 ml) and cooled to 0°C. p-Toluene sulphonic acid monohydrate (24 mg) was added and the mixture was stood at 0°C for 1 hour. The mixture was then allowed to attain room temperature and was stood at room temperature for 6 hours. The mixture was evaporated. The residue was suspended in ethyl acetate (20 ml) and shaken with saturated sodium bicarbonate solution (5 ml). The organic layer was separated and washed with brine. The dried (MgSO4) organic layer was evaporated to give t-butyl 3-β-phenylethyl-7-amino-3-cephem-4-carboxylate (XXV) contaminated with triphenylmethanol as a solid (61 mg). ##SPC6##

Workup

  1. additionwas added
  2. customto attain room temperature
  3. waitwas stood at room temperature for 6 hours
  4. customThe mixture was evaporated
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialThe dried (MgSO4) organic layer
  8. customwas evaporated

Sources & evidence

ORD record
ord-b143069dd41b4f19aa81075b386cf330
Source dataset
uspto-grants-1976_02
Patent number
US03939157

Reaction notes

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