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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
ノート
印刷プレビュー

反応式

HRID 70601 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 67398685HCID 67398685、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 21873804Tetrahydrofuran ethanol溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-0d846df33488401789f3adf4739bf13b
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08822503B2

反応ノート

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