Ethyl orthoformate → (5-Tetrazol-1-yl)-valeric acid ethyl ester

HRID 414748ノート

反応式

HRID 414748 の反応式
[N-:1]=[N+:2]=[N-:3].[Na+].[CH:5](OCC)(OCC)OCC.Cl.[CH2:16]([O:18][C:19](=[O:25])[CH2:20][CH2:21][CH2:22][CH2:23][NH2:24])[CH3:17]>C(O)(=O)C>[CH2:16]([O:18][C:19](=[O:25])[CH2:20][CH2:21][CH2:22][CH2:23][N:24]1[CH:5]=[N:3][N:2]=[N:1]1)[CH3:17]

参加物

5

反応物 3

HCID 31214Ethyl orthoformateHCID 33557Sodium AzideHCID 16094861Ethyl 5-aminopentanoate hydrochloride

生成物 1

HCID 53833799(5-Tetrazol-1-yl)-valeric acid ethyl ester

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

13 g of sodium azide and 59 ml of triethyl orthoformate are added to a solution of 13.4 g of 5-amino-valeric acid ethyl ester hydrochloride in 89 ml of acetic acid and the whole is stirred for 6 hours at 100°. The reaction mixture is cooled and partitioned betwen ethyl acetate and water. The organic phase is washed several times with saturated sodium bicarbonate solution and once with brine and, after drying over sodium sulphate, is concentrated. After purification by chromatography over silica gel (eluant: toluene/ethyl acetate 4:1 to 7:3), the pure title compound is obtained. Rf (toluene/ethyl acetate 1:1); 0.32.

後処理

  1. temperatureThe reaction mixture is cooled
  2. custompartitioned betwen ethyl acetate and water
  3. washThe organic phase is washed several times with saturated sodium bicarbonate solution
  4. dry with materialonce with brine and, after drying over sodium sulphate
  5. concentrationis concentrated
  6. customAfter purification by chromatography over silica gel (eluant: toluene/ethyl acetate 4:1 to 7:3)

出典と根拠

ORDレコード
ord-e4e2e9ce14c942a3a9b7ae5bb059c42a
出典データセット
uspto-grants-1988_12
特許番号
US04794109

反応ノート

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