Water → 3,4-Diethyl-2-azetidinone
Reaction equation
[CH2:1]([CH:3]1[CH:6]([CH2:7][CH3:8])[C:5](=[O:9])[N:4]1S(Cl)(=O)=O)[CH3:2].C1(S)C=CC=CC=1.N1C=CC=CC=1.O>CC(C)=O>[CH2:7]([CH:6]1[CH:3]([CH2:1][CH3:2])[NH:4][C:5]1=[O:9])[CH3:8]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -30 °C
Procedure
(2RS,3RS)-2,3-Diethyl-4-oxoazetidine-1-sulfonyl chloride (step 1) (3.2 g, 14.18 mmol) in acetone (7 ml) was treated with thiophenol (2.92 ml, 28.4 mmol) and cooled to −30° C. Pyridine (1.376 ml, 17.01 mmol) in acetone (2.55 ml) was added dropwise over 30 mins, maintaining the temperature around −30° C. After stirring for 30 minutes, water (10 ml) was added slowly and the mixture was filtered. The filtrate was extracted with diethyl ether (5×25 ml) and the combined organic layers were dried MgSO4, filtered and evaporated to dryness (colorless oil 2.3 g). Purification by chromatography on silica eluting with iso-hexane followed by diethyl ether afforded the title compound;
Workup
- temperaturemaintaining the temperature around −30° C
- filtrationthe mixture was filtered
- extractionThe filtrate was extracted with diethyl ether (5×25 ml)
- filtrationfiltered
- customevaporated to dryness (colorless oil 2.3 g)
- customPurification by chromatography on silica eluting with iso-hexane
Sources & evidence
- ORD record
- ord-ebd48e91b5974b179ab4cd9224afe72a
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08883819B2
Reaction notes
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