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

HRID 414748노트

반응식

HRID 414748 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-e4e2e9ce14c942a3a9b7ae5bb059c42a
출처 데이터셋
uspto-grants-1988_12
특허 번호
US04794109

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