Water → HCID 58452431、化合物

HRID 70689ノート

反応式

HRID 70689 の反応式
Cl[Si](C)(C)C.[I-].[K+].[CH:8]1([C:11]2[CH:12]=[CH:13][C:14]([CH:19]([C:27]3[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH3:35])=[C:29]([F:36])[CH:28]=3)[CH2:20][C@@H:21]3[NH:25][C:24](=[O:26])[CH2:23][CH2:22]3)=[N:15][C:16]=2[O:17]C)[CH2:10][CH2:9]1.O>C(#N)C>[CH:8]1([C:11]2[C:16](=[O:17])[NH:15][C:14]([CH:19]([C:27]3[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH3:35])=[C:29]([F:36])[CH:28]=3)[CH2:20][C@H:21]3[CH2:22][CH2:23][C:24](=[O:26])[NH:25]3)=[CH:13][CH:12]=2)[CH2:10][CH2:9]1

参加物

6

反応物 4

HCID 962WaterHCID 4875Potassium IodideHCID 6397ChlorotrimethylsilaneHCID 67400762(5R)-5-[2-(5-cyclopropyl-6-methoxypyridin-2-yl)-2-(4-ethoxy-3-fluorophenyl)ethyl]pyrrolidin-2-one

生成物 1

HCID 58452431HCID 58452431、化合物

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
50 °C

実験手順

Chlorotrimethylsilane (0.17 mL) and potassium iodide (370 mg) were added to a solution of (5R)-5-[2-(5-cyclopropyl-6-methoxypyridin-2-yl)-2-(4-ethoxy-3-fluorophenyl)ethyl]pyrrolidin-2-one (222 mg) in acetonitrile (4.4 mL) at room temperature, and then the mixture was stirred at 50° C. for one hour. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and filtered, after which the solvent was evaporated under reduced pressure. One diastereomer (A) of the title compound was obtained as a white solid (71 mg, 33% (two steps)) by separating the residue by preparative HPLC (CHIRALPAK IB (20 mm i.d.×250 mm L, Daicel Chemical Industries, LTD.), 40° C., flow rate: 10 mL/min, ethanol:hexane=40:60) and concentrating the fraction eluted with a retention time of 13 minutes. The fraction eluted with a retention time of 28 minutes was concentrated to give the other diastereomer (B) of the title compound as a white solid (71 mg, 33% (two steps)).

後処理

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customafter which the solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-4ce1bb5d0e3a4222a91f6cd07372f579
出典データセット
uspto-grants-2014_09
特許番号
US08822503B2

反応ノート

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