1,1'-(Diazomethylene)bis(benzene) → HCID 70636339, compound

HRID 597493Notes

Reaction equation

HRID 597493 reaction equation
[C:1]1([C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N+]=[N-])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:16][S:17][CH2:18][C:19]1[C@H:24]([C:25]([OH:27])=[O:26])[N:23]2[C:28](=[O:40])[C@@H:29]([NH:30][C:31](=[O:39])[CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C@H:22]2[S:21][CH:20]=1>O1CCOCC1.C(O)(=O)C>[C:1]1([CH:7]([O:27][C:25]([C@@H:24]2[N:23]3[C:28](=[O:40])[C@@H:29]([NH:30][C:31](=[O:39])[CH2:32][C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)[C@H:22]3[S:21][CH:20]=[C:19]2[CH2:18][S:17][CH3:16])=[O:26])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 612301,1'-(Diazomethylene)bis(benzene)HCID 70635663HCID 70635663, compound

Product 1

HCID 70636339HCID 70636339, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of 0.39 g of diphenyldiazomethane in 5 ml of petroleum ether is added dropwise over the course of half an hour to a solution of 0.5 g of 3-methylthiomethyl-7β -phenylacetylamino-2-cephem-4α-carboxylic acid in 20 ml of dioxane, while stirring. The solution is stirred for a further 15 hours at room temperature, treated with a few drops of glacial acetic acid and concentrated under reduced pressure. The residue is recrystallised from methyl acetate and gives pure 3-methylthiomethyl-7β-phenylacetylamino-2-cephem-4α-carboxylic acid diphenylmethyl ester which is dried for 16 hours at room temperature in a high vacuum. Melting point 175-177° C; thin layer chromatogram (silica gel): Rf = 0.77 (system: chloroform/methanol, 1:1); Rf = 0.17 (system: toluene/acetone, 2:1); [α]D20 + 342° ± 1° (c = 1.011 in dioxane); ultraviolet absorption spectrum (in 95% strength aqueous ethanol): λmax = 255 mμ (ε = 7,800) and λmin = 244 mμ (ε = 7,200), infra-red absorption spectrum (in methylene chloride): characteristic bands at 2.92μ, 5.61μ, 5.73μ, 5.92μ, 6.25μ and 6.67μ.

Workup

  1. stirringThe solution is stirred for a further 15 hours at room temperature
  2. concentrationconcentrated under reduced pressure
  3. customThe residue is recrystallised from methyl acetate

Sources & evidence

ORD record
ord-98b24b6e957d481caa96d04c96f8e1dc
Source dataset
uspto-grants-1977_03
Patent number
US04014874

Reaction notes

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