Methanesulfonic Acid → HCID 11053614, compound

HRID 846351Notes

Reaction equation

HRID 846351 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 wre dried over sodium sulfate and concentrated to give 4.87 g (99%) of cis-3-(1-ethoxyethoxy)-4-phenylazetidin-2-one as a colorless oil.

Workup

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

Sources & evidence

ORD record
ord-48f4ff7c861c445c801c9a43f81f9d97
Source dataset
uspto-grants-1992_08
Patent number
US05136060

Reaction notes

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