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

HRID 1727345

반응식

HRID 1727345 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].[CH3:16][CH2:17][CH2:18]CCC.[CH2:22]([Li])[CH2:23][CH2:24][CH3:25].[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:22]([C:23]2[CH:16]=[CH:17][C:18]([O:31][CH3:32])=[CH:25][CH:24]=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 to this was added dropwise a 1.6 M n-butyllithium hexane solution (140 mL, 0.23 mol) with stirring. After completion of the addition, the solution was stirred for 30 minutes at 0° C., then, the solution was 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 addition, the reaction mixture was stirred for 2 hours at room temperature. To the reaction mixture was added water (100 mL) and isopropyl ether (300 mL), and the resulted crude crystal was filtrated. This crude crystal was recrystallized from tetrahydrofuran-hexane to obtain a title compound (23 g, yield: 69%).

후처리

  1. additionAfter completion of the addition
  2. stirringthe solution was stirred for 30 minutes at 0° C.
  3. additionAfter completion of the addition
  4. stirringthe reaction mixture was stirred for 2 hours at room temperature
  5. customthe resulted crude crystal
  6. filtrationwas filtrated
  7. customThis crude crystal was recrystallized from tetrahydrofuran-hexane

출처 및 근거

ORD 기록
ord-ed1d5cbfb8bd42cba4379ff97c1d26a6
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07495018B2

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