Tetrahydrofuran → N-(4-Bromo-2-cyano-5-fluoro-6-hydroxy-3-methylphenyl)-2,2-dimethyl-3-[(phenylmethyl)oxy]propionamide

HRID 17363노트

반응식

HRID 17363 반응식
[O:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:6][C:7]1[C:14]([OH:15])=[C:13]([F:16])[C:12]([Br:17])=[C:11]([CH3:18])[C:8]=1[C:9]#[N:10].[C:19](=[O:22])([O-])O.[Na+]>C(OCC)(=O)C>[Br:17][C:12]1[C:13]([F:16])=[C:14]([OH:15])[C:7]([NH:6][C:19](=[O:22])[C:8]([CH3:11])([CH3:9])[CH2:7][O:1][CH2:5][C:4]2[CH:14]=[CH:13][CH:12]=[CH:2][CH:3]=2)=[C:8]([C:9]#[N:10])[C:11]=1[CH3:18]

참가 물질

5

반응물 3

HCID 8028Tetrahydrofuran2회HCID 516892Sodium BicarbonateHCID 860975142-Amino-5-bromo-4-fluoro-3-hydroxy-6-methylbenzonitrile

생성물 1

HCID 86630841N-(4-Bromo-2-cyano-5-fluoro-6-hydroxy-3-methylphenyl)-2,2-dimethyl-3-[(phenylmethyl)oxy]propionamide수율 70%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

After cooling, the reaction liquid was concentrated under reduced pressure, and azeotroped with benzene. A tetrahydrofuran solution (7 ml) of the resulting residue was dropwise added to a tetrahydrofuran solution (63 ml) of 2-amino-5-bromo-4-fluoro-3-hydroxy-6-methylbenzonitrile (I-75) (3.13 g, 12.77 mmol) and sodium hydrogencarbonate (2.68 g, 31.93 mmol), followed by stirring at room temperature for 19 hours. Ethyl acetate was added to the reaction liquid, followed by washing with water and saturated brine. The organic layer was concentrated under reduced pressure, the resulting residue was dissolved in ethanol (30 ml), aqueous 1 N sodium hydroxide solution (24 ml) was added, followed by stirring at 50° C. for 23 hours. After cooling, the reaction liquid was concentrated under reduced pressure, diluted with ethyl acetate, neutralized with aqueous 1 N hydrochloric acid, washed with saturated brine. The organic layer was concentrated under reduced pressure to obtain the entitled compound (5.82 g, 70%) as a yellow white solid.

후처리

  1. temperatureAfter cooling
  2. customthe reaction liquid
  3. concentrationwas concentrated under reduced pressure
  4. customazeotroped with benzene
  5. washby washing with water and saturated brine
  6. concentrationThe organic layer was concentrated under reduced pressure
  7. dissolutionthe resulting residue was dissolved in ethanol (30 ml)
  8. additionaqueous 1 N sodium hydroxide solution (24 ml) was added
  9. stirringby stirring at 50° C. for 23 hours
  10. temperatureAfter cooling
  11. customthe reaction liquid
  12. concentrationwas concentrated under reduced pressure
  13. additiondiluted with ethyl acetate
  14. washwashed with saturated brine
  15. concentrationThe organic layer was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-c4781a6778eb4504b6f8f268a4146c7c
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737166B2

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