Triethylamine → HCID 14390522, compound

HRID 2351608Notes

Reaction equation

HRID 2351608 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.Cl.[CH3:12][O:13][C:14](=[O:18])[C@@H:15]([CH3:17])[NH2:16].C(N(CC)CC)C>CO>[CH3:12][O:13][C:14](=[O:18])[C@@H:15]([CH3:17])[NH:16][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 796132-Chloro-3-nitropyridineHCID 11182647Methyl D-alaninate hydrochloride

Product 1

HCID 14390522HCID 14390522, compoundYield 5.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 2-chloro-3-nitropyridine (37.76 g, 0.239 mole), (R)-alanine methyl ester hydrochloride (50 g, 0.358 mole) and triethylamine (60.3 g, 0.597 mole) in methanol (370 ml) was refluxed overnight under nitrogen. The solvents were removed under reduced pressure and the resulting solid was triturated in ethyl acetate (300 ml), filtered, and rinsed with additional ethyl acetate. The filtrate and washings were combined and washed once with water. The aqueous wash was extracted with ethyl acetate and the combined organic layers were washed several times with water, dried over sodium sulfate, filtered and evaporated under reduced pressure to give an oil weighing 45.6 g (85%). Elution of a portion of the oil with 1:6 tetrahydrofuran/hexane through a silica gel column gave 3.2 g of product after evaporation of solvent. Drying of a portion of the solid under high vacuum at room temperature gave 0.98 g of title compound, mp 39°-40° C.

Workup

  1. temperaturewas refluxed overnight under nitrogen
  2. customThe solvents were removed under reduced pressure
  3. customthe resulting solid was triturated in ethyl acetate (300 ml)
  4. filtrationfiltered
  5. washrinsed with additional ethyl acetate
  6. washwashed once with water
  7. washThe aqueous wash
  8. extractionwas extracted with ethyl acetate
  9. washthe combined organic layers were washed several times with water
  10. dry with materialdried over sodium sulfate
  11. filtrationfiltered
  12. customevaporated under reduced pressure
  13. customto give an oil
  14. washElution of a portion of the oil with 1:6 tetrahydrofuran/hexane through a silica gel column

Sources & evidence

ORD record
ord-e89a6392a1c24dfda30900c28b1bc21f
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

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