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

HRID 238180Notes

Reaction equation

HRID 238180 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[CH:5][CH:4]=1.[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:17]1([CH:9]([C:6]2[CH:7]=[CH:8][C:3]([CH2:2][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:4][CH:5]=2)[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:21][CH2:20][CH2:19][CH2:18]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 in 147 ml of DMF were stirred 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 evaporated 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. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-e66f71fb0ca244979f4839b900f393b1
Source dataset
uspto-grants-2014_02
Patent number
US08642592B2

Reaction notes

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