Sodium Iodide → Tert-butyl[2-oxo-3-(3,4,5-trifluorophenyl)piperidin-1-yl]carbamate

HRID 599578ノート

反応式

HRID 599578 の反応式
[I-].[Na+].[H-].[Na+].N1(O[CH2:15][CH2:16][CH2:17][CH:18]([C:30]2[CH:35]=[C:34]([F:36])[C:33]([F:37])=[C:32]([F:38])[CH:31]=2)[C:19]([NH:21][NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[O:20])C2C=CC=CC=2N=N1.O.C(=O)(O)[O-].[Na+]>CN(C=O)C.C(OCC)(=O)C>[C:26]([O:25][C:23](=[O:24])[NH:22][N:21]1[CH2:15][CH2:16][CH2:17][CH:18]([C:30]2[CH:35]=[C:34]([F:36])[C:33]([F:37])=[C:32]([F:38])[CH:31]=2)[C:19]1=[O:20])([CH3:29])([CH3:28])[CH3:27]

参加物

7

反応物 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 66839387tert-butyl N'-[5-(benzotriazol-1-yloxy)-2-(3,4,5-trifluorophenyl)pentanoyl]hydrazinecarboxylateHCID 86585896Sodium bicarbonate water

生成物 1

HCID 86628505Tert-butyl[2-oxo-3-(3,4,5-trifluorophenyl)piperidin-1-yl]carbamate収率 44.4%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

Sodium iodide (131 mg) and sodium hydride (containing mineral oil at 40%, 70 mg) were added to a solution of tert-butyl N′-[5-(benzotriazol-1-yloxy)-2-(3,4,5-trifluorophenyl)pentanoyl]hydrazinecarboxylate (420 mg) in DMF (3 mL), and the reaction solution was stirred at 100° C. for 19 hours. The reaction solution was left to cool to room temperature. Ethyl acetate and saturated sodium bicarbonate water were added to the reaction solution, and the organic layer was separated. The resulting organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane→ethyl acetate) to obtain 134 mg of the title compound. The property values of the compound are as follows.

後処理

  1. waitThe reaction solution was left
  2. temperatureto cool to room temperature
  3. customthe organic layer was separated
  4. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (elution solvent: heptane→ethyl acetate)

出典と根拠

ORDレコード
ord-e7bddd6c75b94342bb80388e23378182
出典データセット
uspto-grants-2011_03
特許番号
US07897632B2

反応ノート

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