Potassium Carbonate → HCID 117607192, compound

HRID 588884Notes

Reaction equation

HRID 588884 reaction equation
CS(O[CH:6]1[CH2:9][N:8]([CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7]1)(=O)=O.C([O-])([O-])=O.[K+].[K+].[C:29]([CH:32]1[NH:37][CH2:36][CH2:35][N:34]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:33]1)(=[O:31])[NH2:30]>CC#N>[CH:10]([N:8]1[CH2:9][CH:6]([N:37]2[CH2:36][CH2:35][N:34]([C:38]([O:40][C:41]([CH3:42])([CH3:43])[CH3:44])=[O:39])[CH2:33][CH:32]2[C:29](=[O:31])[NH2:30])[CH2:7]1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonateHCID 11042527Tert-butyl 3-carbamoylpiperazine-1-carboxylate

Product 1

HCID 117607192HCID 117607192, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-benzhydrylazetidin-3-yl methanesulfonate (2.69 g, 8.5 mmol), K2CO3 (1.76 g, 12.8 mmol), tert-butyl 3-carbamoylpiperazine-1-carboxylate (1.95 g, 8.5 mmol) in CH3CN (40 mL) was stirred at reflux for 16 h. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with water and brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (dichloromethane/methanol=50:1) to afford the desired product. (2.08 g, 54% yield).

Workup

  1. temperatureat reflux for 16 h
  2. customThe mixture was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel (dichloromethane/methanol=50:1)

Sources & evidence

ORD record
ord-58f1ad36a6b7430e8d7bc3ac12eb3414
Source dataset
uspto-grants-2016_01
Patent number
US09227978B2

Reaction notes

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