Triethylamine → HCID 15617231, compound

HRID 2351604Notes

Reaction equation

HRID 2351604 reaction equation
C(N(CC)CC)C.Cl[C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][CH:12]=[CH:11][N:10]=1.Cl.[CH2:19]([O:21][C:22](=[O:26])[C@H:23]([CH3:25])[NH2:24])[CH3:20]>C(O)C>[CH2:19]([O:21][C:22](=[O:26])[C@H:23]([CH3:25])[NH:24][C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][CH:12]=[CH:11][N:10]=1)[CH3:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 796132-Chloro-3-nitropyridineHCID 2724356L-Alanine, ethyl ester, hydrochloride (1:1)

Product 1

HCID 15617231HCID 15617231, compoundYield 1.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under a nitrogen atmosphere, triethylamine (82.1 g, 0.813 mole) was added to a stirred suspension of 2-chloro-3-nitropyridine (51.4 g, 0.325 mole) and (S)-alanine ethyl ester hydrochloride (75 g, 0.488 mole) in absolute ethanol (500 ml). After refluxing for 10.5 hr. and stirring at room temperature overnight, the solvents were evaporated under reduced pressure. The residue was triturated in 500 ml of ethyl acetate, filtered, and the filter cake was rinsed with ethyl acetate. The filtrate was washed three times with water, dried over sodium sulfate, filtered and evaporated to an oil weighing 85.6 g. A 1.25-g sample of the oil was eluted through 20 g of silica gel with isopropyl ether as the eluting solvent to give a pure fraction. The solvent was evaporated and the residual oil was dissolved in methylene chloride, filtered, and evaporated to an oil which was dried under high vacuum at 50° C. overnight to give 0.9 g of title compound.

Workup

  1. temperatureAfter refluxing for 10.5 hr
  2. customthe solvents were evaporated under reduced pressure
  3. customThe residue was triturated in 500 ml of ethyl acetate
  4. filtrationfiltered
  5. washthe filter cake was rinsed with ethyl acetate
  6. washThe filtrate was washed three times with water
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated to an oil
  10. washA 1.25-g sample of the oil was eluted through 20 g of silica gel with isopropyl ether as the eluting solvent
  11. customto give a pure fraction
  12. customThe solvent was evaporated
  13. dissolutionthe residual oil was dissolved in methylene chloride
  14. filtrationfiltered
  15. customevaporated to an oil which
  16. customwas dried under high vacuum at 50° C. overnight

Sources & evidence

ORD record
ord-85075752887548c8bff91ce4ffbfabf4
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

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