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

HRID 1062645

반응식

HRID 1062645 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].[CH2:16]([Li])[CH2:17][CH2:18][CH3:19].[CH3:21][CH2:22][CH2:23]CCC.[OH2:27].C([O:31][CH:32](C)C)(C)C>O1CCCC1>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[C:13]([CH2:15][C:16]([C:17]2[CH:21]=[CH:22][C:23]([O:31][CH3:32])=[CH:19][CH:18]=2)=[O:27])[CH:12]=[CH:11][N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 4

HCID 962WaterHCID 7914Diisopropyl EtherHCID 11063648tert-butyl N-(4-methylpyridin-2-yl)carbamateHCID 178418244HCID 178418244, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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 1.6 M n-butyllithium/hexane solution (140 mL, 0.23 mol) was added dropwise with stirring. After completion of the dropwise addition, the mixture was stirred at room temperature for 30 min and cooled to −78° C. A solution of N-(4-methoxybenzoyl)propyleneimine (25 g, 0.13 mol) in anhydrous tetrahydrofuran (50 mL) was added dropwise. After completion of the dropwise addition, the mixture was stirred at room temperature for 2 h. To the reaction mixture were added water (100 mL) and isopropyl ether (300 mL), and the obtained crude crystals were collected by filtration. The crude crystals were recrystallized from tetrahydrofuran-hexane to give the title compound (23 g, yield 69%).

후처리

  1. additionAfter completion of the dropwise addition
  2. stirringthe mixture was stirred at room temperature for 30 min
  3. additionAfter completion of the dropwise addition
  4. stirringthe mixture was stirred at room temperature for 2 h
  5. customthe obtained crude crystals
  6. filtrationwere collected by filtration
  7. customThe crude crystals were recrystallized from tetrahydrofuran-hexane

출처 및 근거

ORD 기록
ord-2e1c2879308049c4b0676845538ff3f4
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06962933B1

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