홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

Hydrogen Bromide → 6-{1-[4-(bromomethyl)phenyl]-2-[(2R)-5-oxopyrrolidin-2-yl]ethenyl}-3-chloropyridin-2(1H)-one

HRID 70624
노트
인쇄 미리보기

반응식

HRID 70624 반응식
[BrH:1].[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([C:11]([C:19]2[CH:24]=[CH:23][C:22]([CH2:25]OCCC(C)C)=[CH:21][CH:20]=2)=[CH:12][C@@H:13]2[NH:17][C:16](=[O:18])[CH2:15][CH2:14]2)=[N:7][C:8]=1[O:9]C.C(=O)(O)[O-].[Na+].O>C(#N)C>[Br:1][CH2:25][C:22]1[CH:23]=[CH:24][C:19]([C:11]([C:6]2[NH:7][C:8](=[O:9])[C:3]([Cl:2])=[CH:4][CH:5]=2)=[CH:12][C@H:13]2[CH2:14][CH2:15][C:16](=[O:18])[NH:17]2)=[CH:20][CH:21]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 260Hydrogen BromideHCID 962WaterHCID 516892Sodium BicarbonateHCID 67398723(5R)-5-[2-(5-chloro-6-methoxypyridin-2-yl)-2-{4-[(3-methylbutoxy)methyl]phenyl}ethenyl]pyrrolidin-2-one

생성물 1

HCID 673960336-{1-[4-(bromomethyl)phenyl]-2-[(2R)-5-oxopyrrolidin-2-yl]ethenyl}-3-chloropyridin-2(1H)-one수율 85%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
70 °C

실험 절차

48% hydrobromic acid (4 mL) was added to a solution of (5R)-5-[2-(5-chloro-6-methoxypyridin-2-yl)-2-{4-[(3-methylbutoxy)methyl]phenyl}ethenyl]pyrrolidin-2-one (E:Z=1:2 mixture) (396 mg) in acetonitrile (4 mL) at room temperature, and the mixture was stirred at 70° C. for three hours. Saturated aqueous sodium bicarbonate and water were sequentially added to the reaction solution at room temperature, followed by extraction with chloroform. The organic layers were dried over anhydrous sodium sulfate and filtered. The solvent was then evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:methanol=50:1→5:1) to give 6-{1-[4-(bromomethyl)phenyl]-2-[(2R)-5-oxopyrrolidin-2-yl]ethenyl}-3-chloropyridin-2(1H)-one (E:Z=1:2 mixture) (321 mg, 85%).

후처리

  1. extractionfollowed by extraction with chloroform
  2. dry with materialThe organic layers were dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customThe solvent was then evaporated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (chloroform:methanol=50:1→5:1)

출처 및 근거

ORD 기록
ord-a28bd9dc718a485b943c6f9a802972c3
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08822503B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트