Potassium Carbonate → 4-(4-{1-(4-Fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxoazetidin-2-yl}phenoxy)butane-1-sulfonic acid

HRID 132750

Reaction equation

HRID 132750 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:11]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20]OCF)=[CH:14][CH:13]=3)[CH:10]([CH2:24][CH2:25][CH:26]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][C:29]=3F)[OH:27])[C:9]2=[O:36])=[C:4](F)[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:44]1[S:49](=[O:51])(=[O:50])[O:48]CC[CH2:45]1>CN(C)C=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:9](=[O:36])[CH:10]([CH2:24][CH2:25][CH:26]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)[OH:27])[CH:11]2[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:45][CH2:44][S:49]([OH:51])(=[O:50])=[O:48])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 154111,4-Butane sultoneHCID 210831331-(4-Fluorofluorophenyl)-3-[3-(4-fluorofluorophenyl)-3-hydroxypropyl]-4-[4-(2-fluoromethoxyethoxy)phenyl]azetidin-2-one

Product 1

HCID 210831414-(4-{1-(4-Fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxoazetidin-2-yl}phenoxy)butane-1-sulfonic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

250 mg of 1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)azetidin-2-one (7) were dissolved in 6 ml of absolute dimethylformamide. 337 mg of powdered potassium carbonate and 69 μl of 1,4, -butanesultone were added. The mixture was stirred at room temperature overnight. The reaction solution was filtered and concentrated under oil pump vacuum. The residue was chromatographed on a 10 g SiO2 cartridge (dichloromethane/methanol=5/1) and crystallized from diethyl ether. The product (131 mg) was obtained as a solid.

Workup

  1. filtrationThe reaction solution was filtered
  2. concentrationconcentrated under oil pump vacuum
  3. customThe residue was chromatographed on a 10 g SiO2 cartridge (dichloromethane/methanol=5/1)
  4. customcrystallized from diethyl ether

Sources & evidence

ORD record
ord-cea232b817344e40b2d3e487fe752c2b
Source dataset
uspto-grants-2008_06
Patent number
US07388004B2

Linked notes

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