Pyridine → Ethyl 3-(butanoylamino)-2-oxobutanoate

HRID 1957950ノート

反応式

HRID 1957950 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

HCID 11736048Ethyl 3-(butanoylamino)-2-oxobutanoate

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 887Methanol溶媒

反応条件

温度
50 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b473d4e6180e41e1a07b8edd0e976cc5
出典データセット
uspto-grants-2013_04
特許番号
US08410098B2

反応ノート

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