Methanesulfonic Acid → HCID 11053614, compound

HRID 1742083Notes

Reaction equation

HRID 1742083 reaction equation
[OH:1][C@H:2]1[C@@H:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[NH:4][C:3]1=[O:12].[CH:13]([O:15][CH2:16][CH3:17])=[CH2:14].CS(O)(=O)=O>C1COCC1.C(=O)(O)[O-].[Na+]>[CH2:13]([O:15][CH:16]([O:1][C@H:2]1[C@@H:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[NH:4][C:3]1=[O:12])[CH3:17])[CH3:14]

Participants

6

Reactant 3

HCID 6395Methanesulfonic AcidHCID 8023Ethyl vinyl etherHCID 10219588cis-3-hydroxy-4-phenylazetidin-2-one

Product 1

HCID 11053614HCID 11053614, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3.41 g (20.9 mmol) of cis-3-hydroxy-4-phenylazetidin-2-one in 15 mL of THF at 0° C. was added 5 mL of ethyl vinyl ether and 20 mg (0.2 mmol) of methanesulfonic acid. The mixture was stirred at 0° C. for 20 min, diluted with 20 mL of saturated aqueous sodium bicarbonate, and extracted with three 40 mL portions of ethyl acetate. The combined ethyl acetate layers were dried over sodium sulfate and concentrated to give 4.87 g (99%) of cis-3-(1-ethoxyethoxy)-4-phenylazetidin-2-one as colorless oil.

Workup

  1. extractionextracted with three 40 mL portions of ethyl acetate
  2. dry with materialThe combined ethyl acetate layers were dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-90cc50fb0021478cb5dc2bbc3c643dad
Source dataset
uspto-grants-1994_08
Patent number
US05336785

Reaction notes

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