Potassium Carbonate → Methyl (4-allylthio-3-ethylazetidin-2-on-1-yl)acetate

HRID 370508Notes

Reaction equation

HRID 370508 reaction equation
[CH2:1]([S:4][CH:5]1[NH:8][C:7](=[O:9])[CH:6]1[CH2:10][CH3:11])[CH:2]=[CH2:3].Br[CH2:13][C:14]([O:16][CH3:17])=[O:15].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:17][O:16][C:14](=[O:15])[CH2:13][N:8]1[CH:5]([S:4][CH2:1][CH:2]=[CH2:3])[CH:6]([CH2:10][CH3:11])[C:7]1=[O:9]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 131064924-Allylthio-3-ethylazetidinone

Product 1

HCID 13106494Methyl (4-allylthio-3-ethylazetidin-2-on-1-yl)acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2.34 g of 4-allylthio-3-ethylazetidinone in 20 ml of redistilled dimethylformamide were added 1.37 ml of methyl bromoacetate and 4.16 g of ground potassium carbonate. The solution was stirred overnight then filtered through a pad of Hyflo, (Hyflo being a Trade Mark), poured into 75 ml of water, and extracted five times with ethyl acetate. The combined organic extracts were washed with water, dried over magnesium sulphate, and evaporated in vacuo to give the title compound. (Yield 3 g)

Workup

  1. filtrationthen filtered through a pad of Hyflo
  2. additionpoured into 75 ml of water
  3. extractionextracted five times with ethyl acetate
  4. washThe combined organic extracts were washed with water
  5. dry with materialdried over magnesium sulphate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-2d84188b4a56427bb449539e0dfcdc04
Source dataset
uspto-grants-1985_07
Patent number
US04526718

Reaction notes

Loading…