Diisopropyl Ether → 1-(4-Methoxyphenyl)-2-(2-tert-butoxycarbonylamino-4-pyridyl)ethanone

HRID 1178573

반응식

HRID 1178573 반응식
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.[CH3:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].C([O:30][CH:31](C)C)(C)C.[O:34]1CCC[CH2:35]1>O>[CH3:35][O:34][C:23]1[CH:22]=[CH:21][C:26]([C:31](=[O:30])[CH2:15][C:13]2[CH:12]=[CH:11][N:10]=[C:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH:14]=2)=[CH:25][CH:24]=1

참가 물질

7

반응물 5

HCID 7914Diisopropyl EtherHCID 8028Tetrahydrofuran2회HCID 8058HexaneHCID 11063648tert-butyl N-(4-methylpyridin-2-yl)carbamateHCID 178418339Butyllithium

생성물 1

HCID 116170921-(4-Methoxyphenyl)-2-(2-tert-butoxycarbonylamino-4-pyridyl)ethanone수율 69%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
-78 °C

실험 절차

A solution of 2-tert-butoxycarbonylamino-4-methylpyridine (20 g, 97 mmol) in anhydrous tetrahydrofuran (300 mL) was cooled to −78° C. and a solution of 1.6 M n-butyllithium in hexane (140 mL, 0.22 mol) was added dropwise with stirring. After complete addition, the mixture was stirred at room temperature for 30 minutes. And then, the mixture was cooled to −78° C. A solution of N-(4-methoxybenzoyl)propyleneimine in anhydrous tetrahydrofuran (50 mL) was added dropwise to the mixture. After complete addition, the mixture was stirred at room temperature for 2 hours. Water (100 mL) and diisopropyl ether (300 mL) were added to the reaction mixture and the resulting crude crystals were collected by filtration. The crude crystals were recrystallized from tetrahydrofuran-hexane to obtain 23 g of the title compound (67 mmol, yield 69%).

후처리

  1. additionAfter complete addition
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  3. additionAfter complete addition
  4. stirringthe mixture was stirred at room temperature for 2 hours
  5. filtrationthe resulting crude crystals were collected by filtration
  6. customThe crude crystals were recrystallized from tetrahydrofuran-hexane

출처 및 근거

ORD 기록
ord-b48b84cf9965492cb367662e8a36f82e
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07276527B2

연결된 노트

불러오는 중…