Ethyl orthoformate → HCID 67517354, compound

HRID 1502138Notes

Reaction equation

HRID 1502138 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 reduced 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 chromatography to give 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 under reduced pressure
  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 chromatography

Sources & evidence

ORD record
ord-442b6ee8a19c40028420f854889c1f35
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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