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4-Toluenesulfonyl chloride → 3-({2-chloro-4-[(E)-2-cyclopentyl-1-(5-methyl-6-oxo-1,6-dihydropyridin-2-yl)ethenyl]phenyl}sulfanyl)propyl 4-methylbenzenesulfonate

HRID 70591
ノート
印刷プレビュー

反応式

HRID 70591 の反応式
Cl.CN(C)C.[CH3:6][C:7]1[CH:12]=[CH:11][C:10]([S:13](Cl)(=[O:15])=[O:14])=[CH:9][CH:8]=1.[Cl:17][C:18]1[CH:19]=[C:20](/[C:29](/[C:36]2[NH:41][C:40](=[O:42])[C:39]([CH3:43])=[CH:38][CH:37]=2)=[CH:30]\[CH:31]2[CH2:35][CH2:34][CH2:33][CH2:32]2)[CH:21]=[CH:22][C:23]=1[S:24][CH2:25][CH2:26][CH2:27][OH:28].CN(C)CCN>C(Cl)(Cl)Cl.O.C(N(CC)CC)C>[CH3:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([O:28][CH2:27][CH2:26][CH2:25][S:24][C:23]2[CH:22]=[CH:21][C:20](/[C:29](/[C:36]3[NH:41][C:40](=[O:42])[C:39]([CH3:43])=[CH:38][CH:37]=3)=[CH:30]\[CH:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)=[CH:19][C:18]=2[Cl:17])(=[O:15])=[O:14])=[CH:9][CH:8]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 73974-Toluenesulfonyl chlorideHCID 66053N,N-DimethylethylenediamineHCID 10313079Trimethylamine HydrochlorideHCID 584526356-[(E)-1-{3-chloro-4-[(3-hydroxypropyl)sulfanyl]phenyl}-2-cyclopentylethenyl]-3-methylpyridin-2(1H)-one

生成物 1

HCID 866580093-({2-chloro-4-[(E)-2-cyclopentyl-1-(5-methyl-6-oxo-1,6-dihydropyridin-2-yl)ethenyl]phenyl}sulfanyl)propyl 4-methylbenzenesulfonate
収率 18%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6212Chloroform溶媒HCID 8471Triethylamine溶媒

実験手順

Triethylamine (148 μL), trimethylamine hydrochloride (50 mg) and 4-methylbenzenesulfonyl chloride (74 mg) were sequentially added to a solution of 6-[(E)-1-{3-chloro-4-[(3-hydroxypropyl)sulfanyl]phenyl}-2-cyclopentylethenyl]-3-methylpyridin-2(1H)-one obtained in Example 1-22 (143 mg) in chloroform (5 mL) under ice-cooling, and the mixture was stirred at room temperature for one hour. Water and N,N-dimethylethylenediamine were added to the reaction solution, followed by extraction with chloroform. The organic layer was sequentially washed with 1 M hydrochloric acid and brine, dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane:ethyl acetate=9:1→1:1) to give 3-({2-chloro-4-[(E)-2-cyclopentyl-1-(5-methyl-6-oxo-1,6-dihydropyridin-2-yl)ethenyl]phenyl}sulfanyl)propyl 4-methylbenzenesulfonate (33 mg, 18%) as a colorless amorphous.

後処理

  1. temperaturecooling
  2. extractionfollowed by extraction with chloroform
  3. washThe organic layer was sequentially washed with 1 M hydrochloric acid and 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 chromatography (hexane:ethyl acetate=9:1→1:1)

出典と根拠

ORDレコード
ord-89ee4b6c089143c485e83945cc23c6db
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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