Cesium carbonate → Tert-Butyl Cyclopentyl{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)methyl]phenyl}-acetate

HRID 877157Notes

Reaction equation

HRID 877157 reaction equation
[C:1]([O:5][C:6](=[O:21])[CH:7]([C:13]1[CH:18]=[CH:17][C:16]([CH2:19]Br)=[CH:15][CH:14]=1)[CH:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[C:22]1([C:28]2[O:29][CH2:30][C:31](=[O:34])[NH:32][N:33]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(=O)(O)[O-].[Na+]>CN(C=O)C>[CH:8]1([CH:7]([C:13]2[CH:18]=[CH:17][C:16]([CH2:19][N:32]3[C:31](=[O:34])[CH2:30][O:29][C:28]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[N:33]3)=[CH:15][CH:14]=2)[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:21])[CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 516892Sodium BicarbonateHCID 142034742-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-5-oneHCID 15225592tert-Butyl 2-(4-(bromomethyl)phenyl)-2-cyclopentylacetate

Product 1

HCID 58074542Tert-Butyl Cyclopentyl{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)methyl]phenyl}-acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8.16 g (23.1 mmol) of tert-butyl[4-(bromomethyl)phenyl](cyclopentyl)acetate, 3.7 g (21 mmol) of 2-phenyl-4H-1,3,4-oxadiazin-5(6H)-one and 7.53 g (23.1 mmol) of cesium carbonate were stirred in 147 ml of DMF at room temperature for 12 h. The reaction solution was then stirred with saturated aqueous sodium bicarbonate solution and extracted twice with ethyl acetate. The combined organic phases were dried over magnesium sulfate and concentrated to dryness under reduced pressure. The crude product obtained was purified chromatographically on silica gel (mobile phase cyclohexane/ethyl acetate 5:1). This gave 6.51 g (14.5 mmol, 69% of theory) of the title compound.

Workup

  1. extractionextracted twice with ethyl acetate
  2. dry with materialThe combined organic phases were dried over magnesium sulfate
  3. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-4191b7084fca4ac8a5c6b004c528665a
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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