Pyridine → 2-isopropyl-2,3-dimethyl-N-(1-(furan-2-yl)ethyl)butanamide

HRID 1183155노트

반응식

HRID 1183155 반응식
N1C=CC=CC=1.[O:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[CH:12]([NH2:14])[CH3:13].[CH:15]([C:18]([CH3:25])([CH:22]([CH3:24])[CH3:23])[C:19](Cl)=[O:20])([CH3:17])[CH3:16]>O1CCCC1>[CH:15]([C:18]([CH3:25])([CH:22]([CH3:24])[CH3:23])[C:19]([NH:14][CH:12]([C:8]1[O:7][CH:11]=[CH:10][CH:9]=1)[CH3:13])=[O:20])([CH3:17])[CH3:16]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 90729alpha-Methyl-2-furanmethanamineHCID 30166072,3-Dimethyl-2-isopropylbutyryl chloride

생성물 1

HCID 666453802-isopropyl-2,3-dimethyl-N-(1-(furan-2-yl)ethyl)butanamide수율 45.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

In a 25 mL round bottom flask, fitted with magnetic stirrer, 15 mL of tetrahydrofuran, 2.1 mmol (1.5 eq.) of pyridine and 1.54 mmol (1.1 eq.) of 1-(furan-2-yl)ethanamine were added. 1.4 mmol of 2-isopropyl-2,3-dimethylbutanoyl chloride (prepared by hydrolysis of 2-isopropyl-N,2,3-trimethylbutanamide, WS-23 with NaNO2 in H2SO4 and subsequent acid chloride formation with SOCl2) were added and the mixture was stirred at room to temperature for 16 hours, overnight. The reaction mixture was extracted with MTBE and HCl (1N in water). The organic layer was washed with NaOH (1N in water) and brine, dried over MgSO4 and concentrated. The crude product was purified by column chromatography, obtaining 160 mg of a beige solid, mp 57-60° C.

후처리

  1. customIn a 25 mL round bottom flask, fitted with magnetic stirrer
  2. extractionThe reaction mixture was extracted with MTBE and HCl (1N in water)
  3. washThe organic layer was washed with NaOH (1N in water) and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography

출처 및 근거

ORD 기록
ord-d023fd8c1d194eafa164c71dc9abbdfe
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08664261B2

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