Sodium hydride → Ethyl 1-[(1R,2S)-2-Fluorocyclopropyl]-6,7,8-trifluoro-5-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 1939267노트

반응식

HRID 1939267 반응식
[F:1][C@H:2]1[CH2:4][C@H:3]1[NH:5][CH:6]=[C:7]([C:13](=[O:25])[C:14]1[C:19]([CH3:20])=[C:18]([F:21])[C:17]([F:22])=[C:16]([F:23])[C:15]=1F)[C:8]([O:10][CH2:11][CH3:12])=[O:9].[H-].[Na+]>O1CCOCC1>[F:1][C@H:2]1[CH2:4][C@H:3]1[N:5]1[C:15]2[C:14](=[C:19]([CH3:20])[C:18]([F:21])=[C:17]([F:22])[C:16]=2[F:23])[C:13](=[O:25])[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6]1

참가 물질

4

반응물 2

HCID 24758Sodium hydrideHCID 178472045HCID 178472045, 화합물

생성물 1

HCID 70250897Ethyl 1-[(1R,2S)-2-Fluorocyclopropyl]-6,7,8-trifluoro-5-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate수율 96.6%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

In 10 ml of anhydrous dioxane was dissolved 1.15 g of ethyl 3-[(1R,2S)-2-fluorocyclopropylamino]-2-(2,3,4,5-tetrafluoro-6-methylbenzoyl)acrylate, and 190 mg of 60% sodium hydride in oil was added thereto, followed by stirring at room temperature for 30 minutes. The dioxane was concentrated to about half the volume, and the concentrate was added to 25 ml of 1N hydrochloric acid under cooling with ice. The crystals precipitated were collected by filtration, washed with diethyl ether, and dried to yield 1.05 g of the titled compound as a yellow crystal.

후처리

  1. additionwas added
  2. concentrationThe dioxane was concentrated to about half the volume
  3. additionthe concentrate was added to 25 ml of 1N hydrochloric acid
  4. temperatureunder cooling with ice
  5. customThe crystals precipitated
  6. filtrationwere collected by filtration
  7. washwashed with diethyl ether
  8. customdried

출처 및 근거

ORD 기록
ord-8947a4fde6144b0d89174b01dfd75f79
출처 데이터셋
uspto-grants-1997_12
특허 번호
US05696132

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