4-Methoxybenzyl azidoformate → 2-Methylene-5-(p-methoxybenzyloxycarbonyl)aminopentanoic acid

HRID 894885ノート

反応式

HRID 894885 の反応式
[CH2:1]=[C:2]([CH2:6][CH2:7][CH2:8][NH2:9])[C:3]([OH:5])=[O:4].[O-2].[Mg+2].[CH3:12][O:13][C:14]1[CH:26]=[CH:25][C:17]([CH2:18][O:19][C:20](N=[N+]=[N-])=[O:21])=[CH:16][CH:15]=1>O.O1CCOCC1>[CH2:1]=[C:2]([CH2:6][CH2:7][CH2:8][NH:9][C:20]([O:19][CH2:18][C:17]1[CH:25]=[CH:26][C:14]([O:13][CH3:12])=[CH:15][CH:16]=1)=[O:21])[C:3]([OH:5])=[O:4]

参加物

6

反応物 3

HCID 1175214-Methoxybenzyl azidoformateHCID 6850729Magnesium monoxideHCID 127744242-Methylene-5-aminopentanoic acid

生成物 1

HCID 135481222-Methylene-5-(p-methoxybenzyloxycarbonyl)aminopentanoic acid収率 105.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

To a solution of 8.8 g of 2-methylene-5-aminopentanoic acid hydrochloric in 100 ml of water is added with stirring 6.36 g of magnesium oxide, followed by a solution of 12.2 g of p-methoxybenzyloxycarbonyl azide in 100 ml of dioxane, and the resulting mixture is stirred at room temperature for two days. The reaction mixture is filtered, and the filtrate diluted with 200 ml of ethyl acetate, two equivalents of Dowex 50 ion exchange resin is added, and the mixture is stirred at room temperature for two hours. The resin is then filtered off and washed with water. The layers in the filtrate are separated and the aqueous layer is extracted twice with ethyl acetate. The combined organic layers are dried and concentrated in vacuo to give 18.2 g of 2-methylene-5-(p-methoxybenzyloxycarbonyl)aminopentanoic acid as an amber oil which crystallizes on standing. This is used without further purification.

後処理

  1. filtrationThe reaction mixture is filtered
  2. additionthe filtrate diluted with 200 ml of ethyl acetate, two equivalents of Dowex 50 ion exchange resin
  3. additionis added
  4. stirringthe mixture is stirred at room temperature for two hours
  5. filtrationThe resin is then filtered off
  6. washwashed with water
  7. customThe layers in the filtrate are separated
  8. extractionthe aqueous layer is extracted twice with ethyl acetate
  9. customThe combined organic layers are dried
  10. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-fea3093f741d404a8a43bcd24d6d45d6
出典データセット
uspto-grants-1981_08
特許番号
US04284779

反応ノート

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