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

HRID 1717517Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1717517
[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

Komponenten

4

Edukt 2

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

Produkt 1

HCID 11786544N-(5-Fluoro-2-phenoxy-phenyl)-N-[2-(2-tosyloxy-ethoxy)-5-methoxy-benzyl]-acetamideAusbeute 74,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-76972d9904ae4cdca0df048fcae3c993
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07803960B2

Notizen zur Reaktion

Wird geladen…