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

HRID 414748Notes

Reaction equation

HRID 414748 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-e4e2e9ce14c942a3a9b7ae5bb059c42a
Source dataset
uspto-grants-1988_12
Patent number
US04794109

Reaction notes

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