Methanol → 3-Formyl-7betaphenylacetylamino-ceph-2-em-4alpha-carboxylic acid diphenylmethyl ester

HRID 2287260Notes

Reaction equation

HRID 2287260 reaction equation
[CH:1]([C:3]1[C@H:8]([C:9]([OH:11])=[O:10])[N:7]2[C:12](=[O:24])[C@@H:13]([NH:14][C:15](=[O:23])[CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C@H:6]2[S:5][CH:4]=1)=[O:2].O1CCOCC1.CO.[C:33]1([C:39]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[N+]=[N-])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C1CCCCC1>[C:33]1([CH:39]([O:10][C:9]([C@@H:8]2[N:7]3[C:12](=[O:24])[C@@H:13]([NH:14][C:15](=[O:23])[CH2:16][C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[C@H:6]3[S:5][CH:4]=[C:3]2[CH:1]=[O:2])=[O:11])[C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 312751,4-DioxaneHCID 612301,1'-(Diazomethylene)bis(benzene)HCID 887161643-Formyl-7beta-phenylacetylamino-ceph-2-em-4alpha-carboxylic acid

Product 1

HCID 113527753-Formyl-7betaphenylacetylamino-ceph-2-em-4alpha-carboxylic acid diphenylmethyl ester

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

A solution of 10 g of 3-formyl-7β-phenylacetylamino-ceph-2-em-4α-carboxylic acid in 250 ml of a 4:1 mixture of dioxane and methanol is treated with a solution of 1.5 mol equivalents of diphenyldiazomethane in cyclohexane. After 2 hours at room temperature, the red-violet solution is evaporated to dryness under reduced pressure. The residue is dissolved in hot methylene chloride; the solution is diluted with cyclohexane whilst warm, and 3-formyl-7βphenylacetylamino-ceph-2-em-4α-carboxylic acid diphenylmethyl ester is obtained in practically quantitative yield in the form of fine colourless felted needles, melting point 175.5°-176° C. (uncorrected, decomposition); [α]D20 =+513°±1° (c=1,084 in chloroform); thin layer chromatogram (silica gel): Rf=0.35 (system: toluene/acetone, 80:20) and Rf=0.58 (system: toluene/acetone 65:35); ultraviolet absorption spectrum (in 95% ethanol): λmax =289 mμ (ε=20,200) and λmin =245 mμ (ε= 2,100); infrared absorption spectrum: characteristic bands at 2.92μ, 3.53μ, 5.59μ, 5.72μ, 5.91μ, 6.34μ, 6.61μ and 6.67μ (in methylene chloride) and at 3.00μ, 5.63μ, 5.76μ, 5.95μ (double band), 5.99μ, 6.07μ and 6.58μ (in mineral oil).

Workup

  1. customthe red-violet solution is evaporated to dryness under reduced pressure
  2. dissolutionThe residue is dissolved in hot methylene chloride
  3. additionthe solution is diluted with cyclohexane
  4. temperaturewhilst warm

Sources & evidence

ORD record
ord-8ecbd09c31d14980b91e78b96df4d3e5
Source dataset
uspto-grants-1981_05
Patent number
US04269977

Reaction notes

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