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

HRID 1062645

反応式

HRID 1062645 の反応式
[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]

参加物

6

反応物 4

HCID 962WaterHCID 7914Diisopropyl EtherHCID 11063648tert-butyl N-(4-methylpyridin-2-yl)carbamateHCID 178418244HCID 178418244、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-2e1c2879308049c4b0676845538ff3f4
出典データセット
uspto-grants-2005_11
特許番号
US06962933B1

関連ノート

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