Pyridine → HCID 11736048, compound

HRID 1957947Notes

Reaction equation

HRID 1957947 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 (9.54 g, 0.06 mol) was dissolved into dried tetrahydrofuran (60 mL), and DMAP (0.24 g, 2.0 mmol) and pyridine (15 mL) were added therein. The mixture was heated for 30 minutes at 50° C., cooled, and slowly dropped with ethyl oxalyl monochloride (16.4 g, 0.12 mol) under an ice bath. After the dropping, the mixture was heated for 4 hours at 70° C., filtered to remove the solid, and evaporated to remove the solvent under reduced pressure. Water (100 mL) was added therein, and the product was extracted with ethyl acetate (120 mL×3). The liquid was separated, and the combined organic phase was washed by water (90 mL) and saturated saline (50 mL×2) respectively, dried over anhydrous sodium sulfate, and rotarily evaporated to remove the solvent. NaHCO3 (3.8 g, 0.045 mol) and methanol (50 mL) were added therein, and the reaction mixture was refluxed for 2 hours, filtered, and evaporated off the solvent under reduced pressure 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. temperatureAfter the dropping, the mixture was heated for 4 hours at 70° C.
  4. filtrationfiltered
  5. customto remove the solid
  6. customevaporated
  7. customto remove the solvent under reduced pressure
  8. additionWater (100 mL) was added
  9. extractionthe product was extracted with ethyl acetate (120 mL×3)
  10. customThe liquid was separated
  11. washthe combined organic phase was washed by water (90 mL) and saturated saline (50 mL×2) respectively
  12. dry with materialdried over anhydrous sodium sulfate
  13. customrotarily evaporated
  14. customto remove the solvent
  15. temperaturethe reaction mixture was refluxed for 2 hours
  16. filtrationfiltered
  17. customevaporated off the solvent under reduced pressure

Sources & evidence

ORD record
ord-4b1cd59386c440998b78c9c7fae91b99
Source dataset
uspto-grants-2013_04
Patent number
US08410098B2

Reaction notes

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