Acetic Acid → 4-[3-[3-(Tert-butyldimethylsilanyloxy)-3-(4-fluorophenyl)propyl]2-(4-methoxyphenyl)-4-oxoazetidin-1-yl]benzonitrile

HRID 2300711Notes

Reaction equation

HRID 2300711 reaction equation
[Si:1]([O:8][CH:9]([C:45]1[CH:50]=[CH:49][C:48]([F:51])=[CH:47][CH:46]=1)[CH2:10][CH2:11][CH:12]([C:31](N1C(C2C=CC=CC=2)COC1=O)=[O:32])[CH:13]([NH:22][C:23]1[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][CH:24]=1)[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C/C(/O[Si](C)(C)C)=N\[Si](C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(O)(=O)C>C(OC)(C)(C)C.O1CCCC1>[Si:1]([O:8][CH:9]([C:45]1[CH:50]=[CH:49][C:48]([F:51])=[CH:47][CH:46]=1)[CH2:10][CH2:11][CH:12]1[C:31](=[O:32])[N:22]([C:23]2[CH:24]=[CH:25][C:26]([C:27]#[N:28])=[CH:29][CH:30]=2)[CH:13]1[C:14]1[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=1)([C:4]([CH3:5])([CH3:7])[CH3:6])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium FluorideHCID 6913588N,O-bis(trimethylsilyl)acetamideHCID 121116194-[5-(Tert-butyldimethylsilanyloxy)-5-(4-fluorophenyl)-1-(4-methoxyphenyl)-2-(2-oxo-4-phenyloxazolidine-3-carbonyl)pentylamino]benzonitrile

Product 1

HCID 121116204-[3-[3-(Tert-butyldimethylsilanyloxy)-3-(4-fluorophenyl)propyl]2-(4-methoxyphenyl)-4-oxoazetidin-1-yl]benzonitrile

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

13.2 g of 4-[5-(tert-butyldimethylsilanyloxy)-5-(4-fluorophenyl)-1-(4-methoxyphenyl)-2-(2-oxo-4-phenyloxazolidine-3-carbonyl)pentylamino]benzonitrile are dissolved in 380 ml of methyl tert-butyl ether, 18.6 ml of N,O-bis(trimethylsilyl)acetamide and 1.86 ml of a 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran are added and the mixture is stirred at room temperature for 2 h. Once the reaction has ended, 10 ml of acetic acid are added, the reaction mixture is concentrated under reduced pressure and the residue is purified on silica gel using toluene/ethyl acetate 50/1. This gives 4-[3-[3-(tert-butyldimethylsilanyloxy)-3-(4-fluorophenyl)propyl]-2-(4-methoxyphenyl)-4-oxoazetidin-1-yl]benzonitrile of molecular weight 544.75 (C32H37FN2O3Si); MS (ESI): 545.56 (M+H+).

Workup

  1. concentrationthe reaction mixture is concentrated under reduced pressure
  2. customthe residue is purified on silica gel

Sources & evidence

ORD record
ord-7391ba3849b647c4bb8753b352a2ea63
Source dataset
uspto-grants-2002_12
Patent number
US06498156B2

Reaction notes

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