p-Toluenesulfonic acid → Benzhydryl 7-salicylideneamino-3-hydroxymethyl-3-cephem-4-carboxylate

HRID 1656185Notes

Reaction equation

HRID 1656185 reaction equation
C1(N[CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)CCCCC1.[CH:14](=[N:22][CH:23]1[C:35](=[O:36])[N:25]2[C:26]([C:32]([OH:34])=[O:33])=[C:27]([CH2:30][OH:31])[CH2:28][S:29][C@H:24]12)[C:15]1[C:16](=[CH:18][CH:19]=[CH:20][CH:21]=1)[OH:17].[C:37]1([CH3:47])[CH:42]=[CH:41][C:40](S(O)(=O)=O)=[CH:39][CH:38]=1>C(OCC)(=O)C>[CH:14](=[N:22][CH:23]1[C:35](=[O:36])[N:25]2[C:26]([C:32]([O:34][CH:47]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[O:33])=[C:27]([CH2:30][OH:31])[CH2:28][S:29][C@H:24]12)[C:15]1[C:16](=[CH:18][CH:19]=[CH:20][CH:21]=1)[OH:17]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 136460587HCID 136460587, compound

Product 1

HCID 136460596Benzhydryl 7-salicylideneamino-3-hydroxymethyl-3-cephem-4-carboxylateYield 91.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a suspension of 7-salicylideneamino-3-hydroxymethyl-3-cephem-4-carboxylic acid dicyclohexylamine salt (3 g) in ethyl acetate (60 ml) was added dropwise an ethyl acetate solution of p-toluenesulfonic acid (1.1 g) with stirring, and the reaction mixture was stirred for an hour at ambient temperature. After the precipitate was filtered off, the filtrate was treated with a solution of excess diphenyldiazomethane in ethyl acetate for an hour. The solvent was distilled off, and the residue was pulverized with diisopropyl ether, collected by filtration and dried to give benzhydryl 7-salicylideneamino-3-hydroxymethyl-3-cephem-4-carboxylate (2.66 g).

Workup

  1. stirringthe reaction mixture was stirred for an hour at ambient temperature
  2. filtrationAfter the precipitate was filtered off
  3. additionthe filtrate was treated with a solution of excess diphenyldiazomethane in ethyl acetate for an hour
  4. distillationThe solvent was distilled off
  5. filtrationcollected by filtration
  6. customdried

Sources & evidence

ORD record
ord-a2e3d592a4204aa0916109a94c837163
Source dataset
uspto-grants-1993_10
Patent number
US05252731

Reaction notes

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