Potassium Carbonate → HCID 21083142, compound

HRID 132749

Reaction equation

HRID 132749 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:31])[CH2:9][CH2:10][CH:11]2[CH:14]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[N:13]([C:23]3[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=3)[C:12]2=[O:30])=[C:4]([F:32])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:39]1[S:44](=[O:46])(=[O:45])[O:43][CH2:42][CH2:41][CH2:40]1>CN(C)C=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:31])[CH2:9][CH2:10][CH:11]2[C:12](=[O:30])[N:13]([C:23]3[CH:24]=[CH:25][C:26]([O:29][CH2:42][CH2:41][CH2:40][CH2:39][S:44]([OH:46])(=[O:45])=[O:43])=[CH:27][CH:28]=3)[CH:14]2[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)=[C:4]([F:32])[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 154111,4-Butane sultoneHCID 210831363-[3-(4-Fluorofluorophenyl)-3-hydroxypropyl]-1-(4-hydroxyphenyl)-4-(4-methoxyphenyl)azetidin-2-one

Product 1

HCID 21083142HCID 21083142, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

160 mg of 3-[3-(4-fluorofluorophenyl)-3-hydroxypropyl]-1-(4-hydroxyphenyl)-4-(4-methoxyphenyl)azetidin-2-one (11) were dissolved in 4 ml of absolute dimethylformamide. 210 mg of powdered potassium carbonate and 42 mg of 1,4,-butanesultone were added. The mixture was stirred at room temperature overnight. The reaction solution was concentrated under oil pump vacuum, taken up in dichloromethane and washed 1× with water. The aqueous phase was acidified with 2N hydrochloric acid and extracted 2× with dichloromethane. The combined organic phases were dried over sodium sulfate and concentrated. The residue was chromatographed on a 10 g SiO2 cartridge (dichloromethane/methanol=5/1). The product (72 mg) was obtained as an oil.

Workup

  1. concentrationThe reaction solution was concentrated under oil pump vacuum
  2. washwashed 1× with water
  3. extractionextracted 2× with dichloromethane
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was chromatographed on a 10 g SiO2 cartridge (dichloromethane/methanol=5/1)

Sources & evidence

ORD record
ord-ccb38761d9384716ae0bc28bb704fc07
Source dataset
uspto-grants-2008_06
Patent number
US07388004B2

Linked notes

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