Triethylamine → HCID 178525077, compound

HRID 2047476Notes

Reaction equation

HRID 2047476 reaction equation
C(OCC)(OCC)OCC.Cl.[NH2:12][C@H:13]1[CH2:18][CH2:17][C@H:16]([C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])[CH2:15][CH2:14]1.C([N:31]([CH2:34]C)CC)C.[N-:36]=[N+:37]=[N-].[Na+]>C(=O)([O-])O.[Na+].C(O)(=O)C>[N:12]1([C@H:13]2[CH2:18][CH2:17][C@H:16]([C:19]([O:21][CH2:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[O:20])[CH2:15][CH2:14]2)[CH:34]=[N:31][N:37]=[N:36]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31214Ethyl orthoformateHCID 33557Sodium AzideHCID 178479264HCID 178479264, compound

Product 1

HCID 178525077HCID 178525077, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of triethyl orthoformate (25 mL) and benzyl trans-4-aminocyclohexanecarboxylate monohydrochloride (1.4 g) were added triethylamine (0.77 mL) and acetic acid (2.0 mL), and the mixture was stirred at 90° C. for 30 min. To this mixture was added sodium azide (1.6 g), and the mixture was stirred at 90° C. for 12 hr. The mixture was cooled, diluted with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine, dried and concentrated under reduced pressure. The residue was washed with hexane, filtered through silica gel (eluted with ethyl acetate), and the filtrate was concentrated to give benzyl trans-4-(1H-tetrazol-1-yl)cyclohexanecarboxylate (0.78 g, 54%) as a white powder.

Workup

  1. stirringthe mixture was stirred at 90° C. for 12 hr
  2. temperatureThe mixture was cooled
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. washThe residue was washed with hexane
  8. filtrationfiltered through silica gel (eluted with ethyl acetate)
  9. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-e28d3cf84af0430ea28ed19500b30688
Source dataset
uspto-grants-2013_11
Patent number
US08592454B2

Reaction notes

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