Acetic Anhydride → N-(5-Fluoro-2-phenoxy-phenyl)-N-[2-(2-tosyloxy-ethoxy)-5-methoxy-benzyl]-acetamide

HRID 1717517노트

반응식

HRID 1717517 반응식
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[C:6]([NH:8][CH2:9][C:10]2[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:11]=2[O:18][CH2:19][CH2:20][O:21][S:22]([C:25]2[CH:31]=[CH:30][C:28]([CH3:29])=[CH:27][CH:26]=2)(=[O:24])=[O:23])[CH:7]=1.[C:39](OC(=O)C)(=[O:41])[CH3:40]>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:32][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)=[C:6]([N:8]([CH2:9][C:10]2[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:11]=2[O:18][CH2:19][CH2:20][O:21][S:22]([C:25]2[CH:31]=[CH:30][C:28]([CH3:29])=[CH:27][CH:26]=2)(=[O:24])=[O:23])[C:39](=[O:41])[CH3:40])[CH:7]=1

참가 물질

4

반응물 2

HCID 7918Acetic AnhydrideHCID 86621789(5-Fluoro-2-phenoxy-phenyl)-(5-methoxy-2-[2-(tosyloxy-)-ethoxy]-benzyl}-amine

생성물 1

HCID 11786544N-(5-Fluoro-2-phenoxy-phenyl)-N-[2-(2-tosyloxy-ethoxy)-5-methoxy-benzyl]-acetamide수율 74.5%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

To a solution of 5.75 g (10.7 mmol) crude 5b in 50 ml pyridine was added 4.37 g (42.8 mmol) acetic acid anhydride. The reaction mixture was stirred over night and poured into ice-cold ethyl acetate. The organic phase was washed with water and brine and were dried with magnesium sulfate. The crude product was purified by silica column chromatography (ethyl acetate:hexane gradient 1:8→1:4). The desired product 5c was obtained in 74.5% yield (4.62 g, 7.97 mmol).

후처리

  1. additionpoured into ice-cold ethyl acetate
  2. washThe organic phase was washed with water and brine
  3. dry with materialwere dried with magnesium sulfate
  4. customThe crude product was purified by silica column chromatography (ethyl acetate:hexane gradient 1:8→1:4)

출처 및 근거

ORD 기록
ord-76972d9904ae4cdca0df048fcae3c993
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07803960B2

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