tert-Butyl methyl ether → 3-[3-[3-(tert-Butyldimethylsilanyloxy)-3-(4-fluorophenyl)propyl]-1-(4-fluorophenyl)-4-oxoazetidin-2-yl]benzonitrile

HRID 2243603Notes

Reaction equation

HRID 2243603 reaction equation
[Si:1]([O:8][CH:9]([C:44]1[CH:49]=[CH:48][C:47]([F:50])=[CH:46][CH:45]=1)[CH2:10][CH2:11][CH:12]([C:30](N1C(C2C=CC=CC=2)COC1=O)=[O:31])[CH:13]([C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[C:25]#[N:26])[NH:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C[Si](C([Si](C)(C)C)C(N)=O)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.COC(C)(C)C>C(O)(=O)C>[Si:1]([O:8][CH:9]([C:44]1[CH:45]=[CH:46][C:47]([F:50])=[CH:48][CH:49]=1)[CH2:10][CH2:11][CH:12]1[C:30](=[O:31])[N:14]([C:15]2[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=2)[CH:13]1[C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[C:25]#[N:26])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 15413tert-Butyl methyl etherHCID 2724141Tetrabutylammonium FluorideHCID 11708267BistrimethylsilylacetamidHCID 222520683-[5-(tert-Butyldimethylsilanyloxy)-5-(4-fluorophenyl)-1-(4-fluorophenylamino)-2-(2-oxo-4-phenyloxazolidine-3-carbonyl)pentyl]benzonitrile

Product 1

HCID 222520763-[3-[3-(tert-Butyldimethylsilanyloxy)-3-(4-fluorophenyl)propyl]-1-(4-fluorophenyl)-4-oxoazetidin-2-yl]benzonitrile

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Under argon, a mixture of 13 g of 3-[5-(tert-butyldimethylsilanyloxy)-5-(4-fluorophenyl)-1-(4-fluorophenylamino)-2-(2-oxo-4-phenyloxazolidine-3-carbonyl)pentyl]benzonitrile 12, 50 ml of bistrimethylsilylacetamide, 0.5 g of tetrabutylammonium fluoride and 100 ml of tert-butyl methyl ether is stirred at room temperature for 10 h. After the reaction has ended, 5 ml of acetic acid are added slowly with ice-cooling, and the mixture is concentrated. The residue is separated by silica gel chromatography (ethyl acetate/heptane=1/8). This gives 13:

Workup

  1. temperaturecooling
  2. concentrationthe mixture is concentrated
  3. customThe residue is separated by silica gel chromatography (ethyl acetate/heptane=1/8)

Sources & evidence

ORD record
ord-30cfbc26c9f74b70915768eea69ad256
Source dataset
uspto-grants-2010_03
Patent number
US07674773B2

Reaction notes

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