Fusaric Acid → 5-Butyl-pyridine-2-carboxylic acid methoxy-methyl-amide

HRID 902015

반응식

HRID 902015 반응식
CN1CCOCC1.C(OC(Cl)=O)C(C)C.[CH3:16][CH2:17][CH2:18][CH2:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]([OH:28])=O)=[N:24][CH:25]=1.Cl.[CH3:30][O:31][NH:32][CH3:33]>C(Cl)Cl>[CH3:30][O:31][N:32]([CH3:33])[C:26]([C:23]1[CH:22]=[CH:21][C:20]([CH2:19][CH2:18][CH2:17][CH3:16])=[CH:25][N:24]=1)=[O:28]

참가 물질

6

반응물 4

HCID 3442Fusaric AcidHCID 79724-Methylmorpholine2회HCID 62365Isobutyl chloroformateHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

생성물 1

HCID 587470075-Butyl-pyridine-2-carboxylic acid methoxy-methyl-amide수율 129.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Add N-methylmorpholine (1.22 mL, 11.1 mmol) and isobutylchloroformate (1.44 mL, 11.1 mmol) to a solution of fusaric acid (2.0 g, 11.1 mmol) in methylene chloride at 0° C. After 15 minutes add O,N-dimethylhydroxylamine hydrochloride (1.1 g, 11.1 mmol) and N-methylmorpholine (1.22 mL, 11.1 mmol). Stir the reaction for at 0° C. 15 minutes and then room temperature for 19 hours. Dilute the reaction with methylene chloride and wash with water (1×50 mL), 10% aqueous citric acid (1×50 mL), brine (1×50 mL), saturated aqueous sodium bicarbonate (1×50 mL), and brine (1×50 mL). Dry the organic solution with sodium sulfate, filter, and concentrate in vacuo to provide the title compound 3.2 g (100%) as a clear yellow oil.

후처리

  1. customthe reaction for at 0° C
  2. additionDilute
  3. washwash with water (1×50 mL), 10% aqueous citric acid (1×50 mL), brine (1×50 mL), saturated aqueous sodium bicarbonate (1×50 mL), and brine (1×50 mL)
  4. dry with materialDry the organic solution with sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate in vacuo

출처 및 근거

ORD 기록
ord-65b54fd4021c4f05b80f48b57b7904b7
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07365066B2

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