Iodoethane → HCID 67160209, compound

HRID 1951218Notes

Reaction equation

HRID 1951218 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][CH2:8][CH2:9][C:10]1[NH:14][N:13]=[N:12][N:11]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:18](I)[CH3:19]>C1COCC1.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:15])[NH:7][CH2:8][CH2:9][C:10]1[N:11]=[N:12][N:13]([CH2:18][CH3:19])[N:14]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 178453348HCID 178453348, compound

Product 1

HCID 67160209HCID 67160209, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of [2-(1H-tetrazol-5-yl)-ethyl]-carbamic acid tert-butyl ester (prepared by the protocols outlined in N. A. Delaney, G. C. Rovnyak and M. Loots, European Patent specification EP 449523) (1.0 g, 4.69 mmol) in dry THF (20 ml) is treated with a 60% dispersion of sodium hydride in mineral oil (0.19 g, 4.69 mmol) and stirred at ambient temperature for 10 minutes. Ethyliodide (0.375 ml, 4.69 mmol) is added and the reaction mixture is heated at reflux for 7 hours, then diluted with ethyl acetate and filtered. The filtrate is evaporated and the residue purified by flash silica chromatography (elution 3:2 hexane/ethyl acetate) to afford the titled compound, [2-(2-ethyl-2H-tetrazol-5-yl)-ethyl]-carbamic acid tert-butyl ester, eluted first and [2-(1-ethyl-1H-tetrazol-5-yl)-ethyl]-carbamic acid tert-butyl ester, eluted second.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureat reflux for 7 hours
  3. filtrationfiltered
  4. customThe filtrate is evaporated
  5. customthe residue purified by flash silica chromatography (elution 3:2 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-dee31644ec3248f19040b4d79eb6a64f
Source dataset
uspto-grants-2013_03
Patent number
US08404684B2

Reaction notes

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