Potassium Carbonate → 1-{2-[4-(4-Ethoxy-phenylethynyl)-phenyl]-1-methyl-ethyl}-3,3-dimethyl-azetidin-2-one

HRID 76197

Reaction equation

HRID 76197 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH:19]([NH2:21])[CH3:20])=[CH:14][CH:13]=2)=[CH:6][CH:5]=1)[CH3:2].C([O-])([O-])=O.[K+].[K+].Cl[CH2:29][C:30]([CH3:35])([CH3:34])[C:31](Cl)=[O:32]>C(#N)C.CN(C1C=CN=CC=1)C>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][C:12]2[CH:13]=[CH:14][C:15]([CH2:18][CH:19]([N:21]3[CH2:29][C:30]([CH3:35])([CH3:34])[C:31]3=[O:32])[CH3:20])=[CH:16][CH:17]=2)=[CH:6][CH:5]=1)[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 613453-Chloro-2,2-dimethylpropanoyl chlorideHCID 666104331-(4-((4-Ethoxyphenyl)ethynyl)phenyl)propan-2-amine

Product 1

HCID 666140781-{2-[4-(4-Ethoxy-phenylethynyl)-phenyl]-1-methyl-ethyl}-3,3-dimethyl-azetidin-2-one

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

To 33.5 mg (120 μmol) 2-[4-(4-ethoxy-phenylethynyl)-phenyl]-1-methyl-ethylamine (I64) in 2.0 mL ACN are added 166 mg (1.20 mmol) K2CO3, a few crystals DMAP and finally 23.5 μL (0.18 mmol) 3-chloropivaloyl chloride (in 1.0 mL ACN). The reaction mixture is stirred at reflux for 6 h. The solvent is removed in vacuo and the residue is resolved EtOAc and washed with water (1×), sat. aq. NaHCO3 solution (2×) and again with water. The organic layer is dried with Na2SO4 and the solvent is evaporated in vacuo. The residue is purified by HPLC (MeOH/H2O/TFA).

Workup

  1. temperatureat reflux for 6 h
  2. customThe solvent is removed in vacuo
  3. washwashed with water (1×), sat. aq. NaHCO3 solution (2×) and again with water
  4. dry with materialThe organic layer is dried with Na2SO4
  5. customthe solvent is evaporated in vacuo
  6. customThe residue is purified by HPLC (MeOH/H2O/TFA)

Sources & evidence

ORD record
ord-dac9277838f3451d989cfe6aa0abe744
Source dataset
uspto-grants-2014_09
Patent number
US08835472B2

Linked notes

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