Pyridine → HCID 11736048, compound

HRID 1957950Notes

Reaction equation

HRID 1957950 reaction equation
[C:1]([NH:6][CH:7]([CH3:11])[C:8]([OH:10])=O)(=[O:5])[CH2:2][CH2:3][CH3:4].[O:12]1[CH2:16][CH2:15]C[CH2:13]1.N1C=CC=CC=1.C([O-])(O)=[O:24].[Na+]>CN(C1C=CN=CC=1)C.CO>[C:1]([NH:6][CH:7]([CH3:11])[C:8](=[O:10])[C:13]([O:12][CH2:16][CH3:15])=[O:24])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 1049PyridineHCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 11194480N-Butyrylalanine

Product 1

HCID 11736048HCID 11736048, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

The compound of formula VI (3.18 g, 0.02 mol) was dissolved into dried tetrahydrofuran (20 mL), and DMAP (0.08 g, 0.6 mmol) and pyridine (5 mL) were added therein. The mixture was heated for 30 minutes at 50° C., cooled, and slowly dropped therein with ethyl oxalyl monochloride (5.46 g, 0.04 mol) under ice bath. After the dropping, the mixture was heated for 4 hours at 70° C., filtered to remove the solid, and evaporated under reduced pressure to remove the solvent. Water (40 mL) was added therein, and the solution was extracted with ethyl acetate (75 mL×3). The liquid was separated, the combined organic phase was washed with water (30 mL) and saturated saline (30 mL×2) respectively, dried over anhydrous sodium sulfate, and rotarily evaporated to remove the solvent therein. NaHCO3 (1.26 g, 0.015 mol) and methanol (20 mL) were added therein, and the mixture was refluxed for 2 hours, filtered, and evaporated under reduced pressure to remove solvent to obtain a yellow oil, i.e., ethyl 3-butyramido-2-oxo-butyrate, which was directly used in the next step without separation.

Workup

  1. additionwere added
  2. temperaturecooled
  3. additionslowly dropped
  4. temperatureAfter the dropping, the mixture was heated for 4 hours at 70° C.
  5. filtrationfiltered
  6. customto remove the solid
  7. customevaporated under reduced pressure
  8. customto remove the solvent
  9. additionWater (40 mL) was added
  10. extractionthe solution was extracted with ethyl acetate (75 mL×3)
  11. customThe liquid was separated
  12. washthe combined organic phase was washed with water (30 mL) and saturated saline (30 mL×2) respectively
  13. dry with materialdried over anhydrous sodium sulfate
  14. customrotarily evaporated
  15. customto remove the solvent
  16. temperaturethe mixture was refluxed for 2 hours
  17. filtrationfiltered
  18. customevaporated under reduced pressure
  19. customto remove solvent

Sources & evidence

ORD record
ord-b473d4e6180e41e1a07b8edd0e976cc5
Source dataset
uspto-grants-2013_04
Patent number
US08410098B2

Reaction notes

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