1-Methyl-3-p-tolyltriazene → 3-Methoxy-7beta-phenylacetylamino-3-cephem-4-carboxylic acid diphenylmethyl ester

HRID 979730Notes

Reaction equation

HRID 979730 reaction equation
[C:1]1([CH:7]([O:14][C:15]([CH:17]2[N:22]3[C:23](=[O:35])[C@@H:24]([NH:25][C:26](=[O:34])[CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C@H:21]3[S:20][CH2:19][C:18]2=[O:36])=[O:16])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:37]N=NNC1C=CC(C)=CC=1>C1C=CC=CC=1>[C:1]1([CH:7]([O:14][C:15]([C:17]2[N:22]3[C:23](=[O:35])[C@@H:24]([NH:25][C:26](=[O:34])[CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C@H:21]3[S:20][CH2:19][C:18]=2[O:36][CH3:37])=[O:16])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 304921-Methyl-3-p-tolyltriazeneHCID 98921957beta-Phenylacetylaminocepham-3-one-4xi-carboxylic acid diphenylmethyl ester

Product 1

HCID 128054463-Methoxy-7beta-phenylacetylamino-3-cephem-4-carboxylic acid diphenylmethyl ester

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 0.050 g of 7β-phenylacetylamino-cepham-3-one-4ξ-carboxylic acid diphenylmethyl ester and 0.020 g of 1-methyl-3-(4-methylphenyl)-triazene in 5 ml of benzene is boiled for 2 hours under reflux. After cooling, the mixture is evaporated under reduced pressure and the residue is purified by thin layer chromatography (silica gel; 1×20 cm; system: toluene/ethyl acetate, 3:1). The zone (Rf~0.18) which is visible under ultraviolet light (λ=254μ) is eluted with acetone and 3-methoxy-7β-phenylacetylamino-3-cephem-4-carboxylic acid diphenylmethyl ester is obtained, ultraviolet absorption spectrum (in ethanol): λmax =264μ (ε=6,300); infrared absorption spectrum (in methylene chloride): Characteristic bands at 2.94μ, 5.63μ, 5.83μ, 5.94μ, 6.26μ and 6.68μ.

Workup

  1. temperatureunder reflux
  2. temperatureAfter cooling
  3. customthe mixture is evaporated under reduced pressure
  4. customthe residue is purified by thin layer chromatography (silica gel; 1×20 cm; system: toluene/ethyl acetate, 3:1)
  5. washis eluted with acetone

Sources & evidence

ORD record
ord-be26a1724939444fad54ccad883df4f4
Source dataset
uspto-grants-1987_05
Patent number
US04668781

Reaction notes

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