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

HRID 1183155ノート

反応式

HRID 1183155 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d023fd8c1d194eafa164c71dc9abbdfe
出典データセット
uspto-grants-2014_03
特許番号
US08664261B2

反応ノート

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