N,N,N-Tributylbutan-1-aminium trifluoroacetate → 4-[3-(3-Hydroxy-3-phenylpropyl)-2-(4-methoxyphenyl)-4-oxoazetidin-1-yl]benzonitrile

HRID 1007074Notes

Reaction equation

HRID 1007074 reaction equation
Br[CH:2]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:3][CH2:4][CH:5]1[C:8](=[O:9])[N:7]([C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)[CH:6]1[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1.FC(F)(F)C([O-])=[O:35].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCOCC1>[OH:35][CH:2]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:3][CH2:4][CH:5]1[C:8](=[O:9])[N:7]([C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)[CH:6]1[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 3084618N,N,N-Tributylbutan-1-aminium trifluoroacetateHCID 226675954-[3-(3-Bromo-3-phenylpropyl)-2-(4-methoxyphenyl)-4-oxoazetidin-1-yl]-benzonitrile

Product 1

HCID 226675944-[3-(3-Hydroxy-3-phenylpropyl)-2-(4-methoxyphenyl)-4-oxoazetidin-1-yl]benzonitrile

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

17 g of 4-[3-(3-bromo-3-phenylpropyl)-2-(4-methoxyphenyl)-4-oxoazetidin-1-yl]-benzonitrile are dissolved in 500 ml of dioxane and, after addition of 34 ml of ˜40 percent tetrabutylammonium trifluoroacetate solution, heated to reflux for 24 h. The mixture was concentrated to about half the volume, mixed with water and methyl tert-butyl ether and separated into the phases. The organic phase is concentrated, and the residue is stirred with 500 ml of ethanol and 200 ml of concentrated ammonia at room temp. for 1 h. It is then again concentrated in vacuo, and the crude product is purified on silica gel with dichloromethane/methanol =30:1 as mobile phase. The alcohol is obtained as an oil. MS (ESI): 413 (M+H+), 395 (M+H+-H2O) [C26H24N2O3 M=412].

Workup

  1. temperatureheated
  2. temperatureto reflux for 24 h
  3. concentrationThe mixture was concentrated to about half the volume
  4. additionmixed with water and methyl tert-butyl ether
  5. customseparated into the phases
  6. concentrationThe organic phase is concentrated
  7. concentrationIt is then again concentrated in vacuo
  8. customthe crude product is purified on silica gel with dichloromethane/methanol =30:1 as mobile phase

Sources & evidence

ORD record
ord-a55de845b5a441349e4519abe81df536
Source dataset
uspto-grants-2004_09
Patent number
US06794359B2

Reaction notes

Loading…