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

HRID 1632877Notes

Reaction equation

HRID 1632877 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-5df31a19a5bf44b4bceb060f681c19c6
Source dataset
uspto-grants-1984_10
Patent number
US04477658

Reaction notes

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