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Hydrochloric Acid → 6-{(E)-1-[3-Chloro-4-(methylsulfanyl)phenyl]-2-[(1S)-3-hydroxycyclopentyl]ethenyl}-3-cyclopropylpyridin-2(1H)-one

HRID 70601
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HRID 70601 반응식
[BH4-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6](/[C:12](/[C:20]2[NH:25][C:24](=[O:26])[C:23]([CH:27]3[CH2:29][CH2:28]3)=[CH:22][CH:21]=2)=[CH:13]\[C@H:14]2[CH2:18][CH2:17][C:16](=[O:19])[CH2:15]2)[CH:7]=[CH:8][C:9]=1[S:10][CH3:11].Cl>C(O)C.O1CCCC1>[Cl:3][C:4]1[CH:5]=[C:6](/[C:12](/[C:20]2[NH:25][C:24](=[O:26])[C:23]([CH:27]3[CH2:29][CH2:28]3)=[CH:22][CH:21]=2)=[CH:13]\[C@H:14]2[CH2:18][CH2:17][CH:16]([OH:19])[CH2:15]2)[CH:7]=[CH:8][C:9]=1[S:10][CH3:11]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 67398685HCID 67398685, 화합물

생성물 1

HCID 584528136-{(E)-1-[3-Chloro-4-(methylsulfanyl)phenyl]-2-[(1S)-3-hydroxycyclopentyl]ethenyl}-3-cyclopropylpyridin-2(1H)-one수율 69.6%

시약·촉매·용매 1

HCID 21873804Tetrahydrofuran ethanol용매

실험 절차

Sodium borohydride (11 mg) was added to a suspension of 6-{(E)-1-[3-chloro-4-(methylsulfanyl)phenyl]-2-[(1S)-3-oxocyclopentyl]ethenyl}-3-cyclopropylpyridin-2(1H)-one obtained in Example 1-71 (50 mg) in ethanol-tetrahydrofuran (2.5 mL, 4:1) under ice-cooling, and the mixture was stirred at room temperature for 30 minutes. The reaction solution was poured into 0.5 M hydrochloric acid, followed by extraction with chloroform. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=10:0→9:1) to give the title compound (35 mg, 60%) as a colorless amorphous.

후처리

  1. temperaturecooling
  2. extractionfollowed by extraction with chloroform
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent was then evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (chloroform:methanol=10:0→9:1)

출처 및 근거

ORD 기록
ord-0d846df33488401789f3adf4739bf13b
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08822503B2

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