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

HRID 1717512Notes

Reaction equation

HRID 1717512 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][C:13]=1[CH2:14][NH:15][C:16]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=1[O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:36](OC(=O)C)(=[O:38])[CH3:37]>N1C=CC=CC=1>[CH2:1]([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][C:13]=1[CH2:14][N:15]([C:16]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=1[O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:36](=[O:38])[CH3:37])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 67104233[2-(2-Benzyloxy-ethoxy)-5-methoxy-benzyl]-(5-fluoro-2-phenoxy-phenyl)-amine

Product 1

HCID 24785291N-[2-(2-benzyloxy-ethoxy)-5-methoxy-benzyl]-N-(5-fluoro-2-phenoxy-phenyl)-acetamideYield 79%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 5.08 g (10.7 mmol) crude 2b in 50 ml 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, diluted aqueous sodium hydrogen sulfate, 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 2c was obtained in 79% yield (4.36 g, 8.45 mmol).

Workup

  1. additionpoured into ice-cold ethyl acetate
  2. washThe organic phase was washed with water, diluted aqueous sodium hydrogen sulfate, 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-e33712224bc24f14a3063b40cb14cc4d
Source dataset
uspto-grants-2010_09
Patent number
US07803960B2

Reaction notes

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