Pyridine → N-[1-(2-Benzyloxy-ethyl)-2-oxo-propyl]-4-bromo-2-fluoro-benzamide

HRID 1445762노트

반응식

HRID 1445762 반응식
[C:1](OC(=O)C)(=O)C.N1C=CC=CC=1.[CH2:14]([O:21][CH2:22][CH2:23][CH:24]([NH:28][C:29](=[O:38])[C:30]1[CH:35]=[CH:34][C:33]([Br:36])=[CH:32][C:31]=1[F:37])[C:25]([OH:27])=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[CH2:14]([O:21][CH2:22][CH2:23][CH:24]([NH:28][C:29](=[O:38])[C:30]1[CH:35]=[CH:34][C:33]([Br:36])=[CH:32][C:31]=1[F:37])[C:25](=[O:27])[CH3:1])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

참가 물질

4

반응물 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 589514334-Benzyloxy-2-(4-bromo-2-fluoro-benzoylamino)-butyric acid2회

생성물 1

HCID 58951463N-[1-(2-Benzyloxy-ethyl)-2-oxo-propyl]-4-bromo-2-fluoro-benzamide

반응 조건

온도
90 °C

실험 절차

Add acetic anhydride (0.97 mmol) and pyridine (0.58 mmol) to a round bottom flask containing 4-benzyloxy-2-(4-bromo-2-fluoro-benzoylamino)-butyric acid (1.0 mmol) (See Intermediate 35) and heat to 90° C. for two hours. After this time, remove the heat and concentrate in vacuo. Wash crude with 1N hydrochloric acid and water while extracting with diethyl ether. Concentrate the organics in vacuo and purify on an Isco CombiFlash® chromatography system eluting with ethyl acetate and hexane. MS (m/e) (79Br/81Br): 408.3/410.3 (M+1)

후처리

  1. customAfter this time, remove the
  2. temperatureheat
  3. concentrationconcentrate in vacuo
  4. washWash crude with 1N hydrochloric acid and water
  5. extractionwhile extracting with diethyl ether
  6. concentrationConcentrate the organics in vacuo
  7. custompurify on an Isco CombiFlash® chromatography system
  8. washeluting with ethyl acetate and hexane

출처 및 근거

ORD 기록
ord-8a6c132dd22447289cb3cd365b804427
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07666871B2

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