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Butane, 1-diazo- → 3-n-Butoxy-7beta-phenylacetylamino-3-cephem-4-carboxylic acid diphenylmethyl ester

HRID 1995803
ノート
印刷プレビュー

反応式

HRID 1995803 の反応式
[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.[N+](=[CH:39][CH2:40][CH2:41][CH3:42])=[N-]>CO.C(OCC)C>[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][CH2:39][CH2:40][CH2:41][CH3:42])=[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 164728Butane, 1-diazo-HCID 98921957beta-Phenylacetylaminocepham-3-one-4xi-carboxylic acid diphenylmethyl ester

生成物 1

HCID 127841623-n-Butoxy-7beta-phenylacetylamino-3-cephem-4-carboxylic acid diphenylmethyl ester

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 3283Diethyl Ether溶媒

反応条件

温度
0 °C

実験手順

A solution, cooled to 0° C., of 2.0 g of 7β-phenylacetylamino-cepham-3-one-4ξ-carboxylic acid diphenylmethyl ester in 75 ml of methanol is treated with excess diazo-n-butane in diethyl ether. The mixture is stirred for 15 minutes at 0° C. and is then evaporated under reduced pressure. The oily residue is purified by means of preparative thin layer chromatography (silica gel plates, 6×100 cm; system: toluene/ethyl acetate, 3:1). The layer which is visible under ultraviolet light (λ=254 mμ) is removed and in each case eluted with acetone. This zone (Rf~0.33) yields 3-n-butoxy-7β-phenylacetylamino-3-cephem-4-carboxylic acid diphenylmethyl ester which after crystallisation from a mixture of methylene chloride and diethyl ether is in the form of colourless flakes which melt at 168°-170° C., [α]D20 =+55°±1° (c=0.38 in chloroform); ultraviolet absorption spectrum (in 95% strength aqueous ethanol): λmax =264 mμ (ε=7,300); infrared absorption spectrum (in methylene chloride): characteristic bands at 2.98μ, 5.62μ, 5.81μ, 5.92μ, 6.25μ and 6.62μ.

後処理

  1. customis then evaporated under reduced pressure
  2. customThe oily residue is purified by means of preparative thin layer chromatography (silica gel plates, 6×100 cm; system: toluene/ethyl acetate, 3:1)
  3. customis removed and in each case
  4. washeluted with acetone

出典と根拠

ORDレコード
ord-6363a8921ff24f51aea8f6268d9fe0e5
出典データセット
uspto-grants-1983_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04405778

反応ノート

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