Ethyl orthoformate → HCID 67517354, compound

HRID 2173364Notes

Reaction equation

HRID 2173364 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([CH:9]([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.[CH:16](OCC)(OCC)OCC.[N-:26]=[N+:27]=[N-:28].[Na+]>CC(O)=O>[CH3:8][C:6]1[C:5]([CH:9]([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=[C:2]([N:1]2[CH:16]=[N:28][N:27]=[N:26]2)[N:7]=1

Participants

5

Reactant 3

HCID 31214Ethyl orthoformateHCID 33557Sodium AzideHCID 67515686HCID 67515686, compound

Product 1

HCID 67517354HCID 67517354, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of ethyl 2-(6-amino-2-methylpyridin-3-yl)propanoate (1.6 g, 7.6 mmol), CH(OEt)3 (3.4 g, 22.8 mmol) in AcOH (50 mL) was added NaN3 (0.6 g, 9.2 mmol) at room temperature. The mixture was heated to 90° C. and stirred for 50 min. The mixture was cooled to ambient temperature and stand over night. The mixture was concentrated under reduce pressure. Water was added, and the mixture was extracted with EtOAc. The combined organic layer was washed with brine, dried over anhydrous Na2SO4, concentrated and the residue was purified by column chromatograph to give compound ethyl 2-[2-methyl-6-(1H-tetrazol-1-yl)pyridin-3-yl]propanoate.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. waitstand over night
  3. concentrationThe mixture was concentrated
  4. additionWater was added
  5. extractionthe mixture was extracted with EtOAc
  6. washThe combined organic layer was washed with brine
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated
  9. customthe residue was purified by column chromatograph

Sources & evidence

ORD record
ord-ddaaacc35c0d457ba77bdd256bc2a2f5
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

Loading…