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

HRID 1717517Notes

Reaction equation

HRID 1717517 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-76972d9904ae4cdca0df048fcae3c993
Source dataset
uspto-grants-2010_09
Patent number
US07803960B2

Reaction notes

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