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Water → (3RS,4RS)-4-[3-oxo-3-(3-fluoro-6-methoxyquinolin-4-yl)-propyl]-1-[2-(2,5-difluoro-phenylsulfanyl)ethyl]piperidine-3-acetic acid

HRID 1767098
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HRID 1767098 반응식
[O:1]=[C:2]([C:27]1[C:36]2[C:31](=[CH:32][CH:33]=[C:34]([O:37][CH3:38])[CH:35]=2)[N:30]=[CH:29][C:28]=1[F:39])[CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][S:13][C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=2[F:21])[CH2:7][CH:6]1[CH2:22][C:23]([O:25]C)=[O:24].[OH-].[Na+].O1CCOCC1.O>C(OCC)C>[O:1]=[C:2]([C:27]1[C:36]2[C:31](=[CH:32][CH:33]=[C:34]([O:37][CH3:38])[CH:35]=2)[N:30]=[CH:29][C:28]=1[F:39])[CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][S:13][C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=2[F:21])[CH2:7][CH:6]1[CH2:22][C:23]([OH:25])=[O:24]
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참가 물질

6

반응물 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 86589522methyl (3RS,4RS)-4-[3-oxo-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,5-difluorophenylsulfanyl)ethyl]piperidine-3-acetate

생성물 1

HCID 10256889(3RS,4RS)-4-[3-oxo-3-(3-fluoro-6-methoxyquinolin-4-yl)-propyl]-1-[2-(2,5-difluoro-phenylsulfanyl)ethyl]piperidine-3-acetic acid수율 78.6%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

반응 조건

온도
20 °C

실험 절차

A mixture of 0.3 g of methyl (3RS,4RS)-4-[3-oxo-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2,5-difluorophenylsulfanyl)ethyl]piperidine-3-acetate in 1.34 cm3 of a 1N aqueous sodium hydroxide solution and 5 cm3 of dioxane is brought to a temperature in the region of 60° C. with stirring and under an inert atmosphere for 1 hour. After cooling to around 20° C., the reaction medium is evaporated to dryness under reduced pressure (2 kPa) at a temperature in the region of 50° C. The evaporation residue obtained is taken up with 20 cm3 of water and 20 cm3 of diethyl ether, and the aqueous phase is separated after settling out and neutralized with 1.3 cm3 of 1N aqueous hydrochloric acid solution and is then extracted with 70 cm3 of ethyl acetate. The organic phase is dried over magnesium sulfate, filtered, and then evaporated according to the same conditions above. 0.23 g of (3RS,4RS)-4-[3-oxo-3-(3-fluoro-6-methoxyquinolin-4-yl)-propyl]-1-[2-(2,5-difluoro-phenylsulfanyl)ethyl]piperidine-3-acetic acid, in the form of a beige-colored solid, is obtained.

후처리

  1. customis brought to a temperature in the region of 60° C.
  2. customthe reaction medium is evaporated to dryness under reduced pressure (2 kPa) at a temperature in the region of 50° C
  3. customThe evaporation residue obtained
  4. customthe aqueous phase is separated
  5. extractionis then extracted with 70 cm3 of ethyl acetate
  6. dry with materialThe organic phase is dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

출처 및 근거

ORD 기록
ord-890d12028b36410f841c743427533164
출처 데이터셋
uspto-grants-2007_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07232834B2

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