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

HRID 1462053
ノート
印刷プレビュー

反応式

HRID 1462053 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8078
Cyclohexane
溶媒

実験手順

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-7β-phenylacetylamino-ceph-2-em-4α-carboxlic 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).

後処理

  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

出典と根拠

ORDレコード
ord-98a1ffdf7c644b3fa02a1795845764e8
出典データセット
uspto-grants-1984_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04458069

反応ノート

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