Pyridine → Ethyl 3-acetamido-2-oxobutanoate

HRID 444820

반응식

HRID 444820 반응식
[C:1]([NH:4][C@H:5]([C:7]([OH:9])=O)[CH3:6])(=[O:3])[CH3:2].N1C=CC=CC=1.[C:16]([O:19][CH2:20][CH3:21])(=[O:18])C>C1COCC1.CN(C)C1C=CN=CC=1>[C:1]([NH:4][CH:5]([CH3:6])[C:7](=[O:9])[C:16]([O:19][CH2:20][CH3:21])=[O:18])(=[O:3])[CH3:2]

참가 물질

6

반응물 3

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 88064N-Acetyl-L-alanine

생성물 1

HCID 22245807Ethyl 3-acetamido-2-oxobutanoate

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 8028Tetrahydrofuran용매

실험 절차

52 g (396 mmol) of acetylalanine were dissolved in 800 ml of THF, and 45 mg (0.4 mmol) of 4-dimethylaminopyridine and 96 ml (1188 mmol) of pyridine were added. The mixture was heated to reflux, and 88 ml (792 mmol) of ethyl oxalyl chloride were added dropwise over a period of 45 min. The mixture was stirred at reflux for a further 3 h. The reaction mixture was added to ice-water, ethyl acetate was added and the mixture was extracted. The organic phase was washed with saturated aqueous sodium chloride solution, dried over sodium sulfate and concentrated on a rotary evaporator. The crude mixture was reacted further without any further purification.

후처리

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. temperatureat reflux for a further 3 h
  4. additionwas added
  5. extractionthe mixture was extracted
  6. washThe organic phase was washed with saturated aqueous sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated on a rotary evaporator
  9. customThe crude mixture was reacted further without any further purification

출처 및 근거

ORD 기록
ord-027f0eee200345f99a13e2b6ceafb7ee
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476267B2

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