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

HRID 622809Notes

Reaction equation

HRID 622809 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+].O>CN(C)C=O>[CH2:1]([S:4][CH:5]1[N:8]([CH2:13][C:14]([O:16][CH3:17])=[O:15])[C:7](=[O:9])[CH:6]1[CH2:10][CH3:11])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 962WaterHCID 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 vigorously stirred solution of 2.34 g of 4-allylthio-3-ethylazetidin-2-one in 20 ml of dimethylformamide were added 1.37 ml of methyl bromoacetate and 4.16 g of finely ground potassium carbonate. After 18 hours, the mixture was poured into 75 ml of water, was extracted into ethyl acetate (5×20 ml) and the combined organic extracts were washed with water (6×15 ml), dried over MgSO4 and evaporated in vacuo to dryness. Chromatography over silica gel, eluting with hexane-ethyl acetate mixtures, afforded the title compound as a yellow oil (3 g).

Workup

  1. extractionwas extracted into ethyl acetate (5×20 ml)
  2. washthe combined organic extracts were washed with water (6×15 ml)
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo to dryness
  5. washChromatography over silica gel, eluting with hexane-ethyl acetate mixtures

Sources & evidence

ORD record
ord-c918aacba41144988c8e522086e58752
Source dataset
uspto-grants-1988_09
Patent number
US04772692

Reaction notes

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