Hydrochloric Acid → 3-(4'-Chloro-3'-fluoro-4-methylbiphenyl-3-yl)-8,8-difluoro-4-hydroxy-1-azaspiro[4.5]dec-3-en-2-one

HRID 1466458노트

반응식

HRID 1466458 반응식
CC(C)([O-])C.[K+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[C:16]([CH2:21][C:22]([NH:24][C:25]3([C:33]([O:35]C)=O)[CH2:30][CH2:29][C:28]([F:32])([F:31])[CH2:27][CH2:26]3)=[O:23])[CH:15]=2)=[CH:10][C:9]=1[F:37].Cl>CN(C)C=O>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[C:16]([C:21]3[C:22](=[O:23])[NH:24][C:25]4([CH2:30][CH2:29][C:28]([F:31])([F:32])[CH2:27][CH2:26]4)[C:33]=3[OH:35])[CH:15]=2)=[CH:10][C:9]=1[F:37]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxideHCID 86707849Methyl 1-{[(4'-chloro-3'-fluoro-4-methylbiphenyl-3-yl)acetyl]amino}-4,4-difluorocyclohexanecarboxylate

생성물 1

HCID 601490113-(4'-Chloro-3'-fluoro-4-methylbiphenyl-3-yl)-8,8-difluoro-4-hydroxy-1-azaspiro[4.5]dec-3-en-2-one

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Under nitrogen 2.23 g (19.9 mmol) of potassium tert-butoxide were added to 8.19 g (18.0 mmol) of the compound from Example 5A in 80 ml of N,N-dimethylformamide. The reaction mixture was stirred at room temperature for 15 minutes. The reaction mixture was then added to ice-water, 1N aqueous hydrogen chloride solution was added dropwise until a pH of 1-2 had been reached, the mixture was stirred for 30 minutes and filtered off with suction, the filter cake was washed with water and the precipitate was dried. For further purification, the product was dissolved in 1N aqueous sodium hydroxide solution, precipitated by acidification with aqueous 1 N hydrochloric acid, stirred for 30 minutes, washed with water, filtered off and dried. This gave 7.50 g (97% of theory) of the title compound.

후처리

  1. additionwas added dropwise until a pH of 1-2
  2. stirringthe mixture was stirred for 30 minutes
  3. filtrationfiltered off with suction
  4. washthe filter cake was washed with water
  5. customthe precipitate was dried
  6. customFor further purification
  7. dissolutionthe product was dissolved in 1N aqueous sodium hydroxide solution
  8. customprecipitated by acidification with aqueous 1 N hydrochloric acid
  9. stirringstirred for 30 minutes
  10. washwashed with water
  11. filtrationfiltered off
  12. customdried

출처 및 근거

ORD 기록
ord-90ea17bb6e0a4decbfa30388d612669b
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09000026B2

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