Reaction equation
C(O[C:4](=[O:11])[CH2:5][N:6]([CH2:9][CH3:10])[CH2:7][CH3:8])C.[CH:12](=CN)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Cl-].[NH4+:22].[CH:23]1C=CC=CC=1>C(OCC)C>[CH3:23][N:22]1[C@@H:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@H:5]([N:6]([CH2:7][CH3:8])[CH2:9][CH3:10])[C:4]1=[O:11]Participants
Procedure
2.95 g (10 mmoles) of the ethylzinc enolate lithium chloride complex of N,N-diethylglycine ethyl ester (the product obtained from example I) was dissolved in 20 ml benzene at room temperature. To this clear colourless solution was added 1.19 g (10 mmoles) of N-(benzylidene)methylamine. The resulting solution was refluxed for 30 min. During this period some precipitate formed. The reaction mixture was cooled to room temperature and diluted with 25 ml diethyl ether. To this mixture, 10 ml of a saturated aqueous ammonium-chloride solution was added. The aqueous layer was separated and the organic layer was twice washed with 10 ml of an aqueous ammonium chloride solution and twice with 10 ml portions of water, dried over sodium sulfate and concentrated in vacuo yielding 2.2 g (95%) of the 2-azetidinone product as a white solid with the properties: m.p. 70°-71° C. 1H NMR (60 MHz, CDCl3): δ7.30 (m, 5H, arom.), 4.60 (d, J=1.6 Hz, 1H, NCHCHPh), 4.10 (d, J=1.6 Hz, 1H, NCHCHPh), 2.90 (s, 3H, NCH3), 2.90 (q, 4H, NCH2CH3), 1.15 (t, 6H, NCH2CH3).
Workup
- temperatureThe resulting solution was refluxed for 30 min
- customDuring this period some precipitate formed
- customThe aqueous layer was separated
- washthe organic layer was twice washed with 10 ml of an aqueous ammonium chloride solution and twice with 10 ml portions of water
- dry with materialdried over sodium sulfate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-230bca7aec914bceacdf0b22d937f7a7
- Source dataset
- uspto-grants-1990_02
- Patent number
- US04898955
Linked notes
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