Acetic Anhydride → Ethyl 2-acetamido-3-oxobutanoate

HRID 75489노트

반응식

HRID 75489 반응식
O[N:2]=[C:3]([C:9](=[O:11])[CH3:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:12](OC(=O)C)(=[O:14])[CH3:13]>CCO.[Pd]>[C:12]([NH:2][CH:3]([C:9](=[O:11])[CH3:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5])(=[O:14])[CH3:13]

참가 물질

5

반응물 2

HCID 7918Acetic Anhydride2회HCID 178472877HCID 178472877, 화합물2회

생성물 1

HCID 224840Ethyl 2-acetamido-3-oxobutanoate수율 86.6%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

To a mixture of ethyl 2-(hydroxyimino)-3-oxobutanoate (compound 8, 9.32 g, 58.5 mmol), Pd/C (400 mg, palladium on carbon, 10 wt %, support activated carbon, wet, Degussa type E101 NE/W) in EtOH was added acetic anhydride (compound 9, 11.0 mL, 117.0 mmol) at room temperature. The reaction mixture was stirred at room temperature under H2 for 15 hrs. The palladium was filtered off (filter aid, Celite 521 AW), then the filtrate was concentrated in vacuo. The crude product was purified by flash column chromatography (Biotage SP1™ FLASH Purification System was used for normal phase column chromatography with tetrahydrofuran and hexane) to provide the title compound (9.48 g, 86%) as a white solid.

후처리

  1. filtrationThe palladium was filtered off
  2. filtration(filter aid, Celite 521 AW)
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe crude product was purified by flash column chromatography (Biotage SP1™ FLASH Purification System was used for normal phase column chromatography with tetrahydrofuran and hexane)

출처 및 근거

ORD 기록
ord-861d163c6b48453d9e563453ad702c74
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835436B2

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