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

HRID 1009368노트

반응식

HRID 1009368 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-634406813c9444d8a5081b21ac3a58ad
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07973033B2

반응 노트

불러오는 중…