Acetic Acid → 4-[3-[3-(4-Fluorophenyl)-3-hydroxypropyl]-2-(4-methoxyphenyl)4-oxoazetidin-1-yl]benzonitrile

HRID 2105720Notes

Reaction equation

HRID 2105720 reaction equation
[Si]([O:8][CH:9]([C:33]1[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=1)[CH2:10][CH2:11][CH:12]1[C:15](=[O:16])[N:14]([C:17]2[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=2)[CH:13]1[C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1)(C(C)(C)C)(C)C.C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[F:39][C:36]1[CH:35]=[CH:34][C:33]([CH:9]([OH:8])[CH2:10][CH2:11][CH:12]2[C:15](=[O:16])[N:14]([C:17]3[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=3)[CH:13]2[C:25]2[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=2)=[CH:38][CH:37]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium Fluoride2×HCID 121116204-[3-[3-(Tert-butyldimethylsilanyloxy)-3-(4-fluorophenyl)propyl]2-(4-methoxyphenyl)-4-oxoazetidin-1-yl]benzonitrile

Product 1

HCID 121116214-[3-[3-(4-Fluorophenyl)-3-hydroxypropyl]-2-(4-methoxyphenyl)4-oxoazetidin-1-yl]benzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3.5 g of 4-[3-[3-(tert-butyldimethylsilanyloxy)-3-(4-fluorophenyl)propyl]-2-(4-methoxyphenyl)-4-oxoazetidin-1-yl]-benzonitrile (3) were dissolved in 65 ml of tetrahydrofuran. 0.74 ml of acetic acid and 8.03 ml of a 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran were added and the mixture was stirred at room temperature for 2 h. Another 4.82 ml of the tetrabutylammonium fluoride solution were then added, and the mixture was stirred at reflux temperature for another 3 h. The cooled reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel chromatography using n-heptane/ethyl acetate 2/1. This produced 4-[3-[3-(4-fluorophenyl)-3-hydroxypropyl]-2-(4-methoxyphenyl)-4-oxoazetidin-1-yl]-benzonitrile (4) of molecular weight 430.48 (C26H23FN2O3); MS ESI): 431.24 (M+H+).

Workup

  1. stirringthe mixture was stirred
  2. temperatureat reflux temperature for another 3 h
  3. customThe cooled reaction mixture
  4. concentrationwas concentrated under reduced pressure
  5. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-0881b0d27376482ba115efa56b748899
Source dataset
uspto-grants-2009_08
Patent number
US07579339B2

Reaction notes

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