Sodium Carbonate → 4-Nitrobenzyl-(4-allylthio-3-ethylazetidin-2-on-1-yl) acetate
Reaction equation
[CH2:1]([S:4][CH:5]1[N:8](CC(O)=O)[C:7](=[O:13])[CH:6]1[CH2:14][CH3:15])[CH:2]=[CH2:3].[C:16](=[O:19])([O-])[O-:17].[Na+].[Na+].[N+:22]([C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Br)=[CH:27][CH:26]=1)([O-:24])=[O:23].[CH3:33]C(N(C)C)=O>>[C:16]([O:17][N:8]1[CH:5]([S:4][CH2:1][CH:2]=[CH2:3])[C:6]([CH2:29][C:28]2[CH:31]=[CH:32][C:25]([N+:22]([O-:24])=[O:23])=[CH:26][CH:27]=2)([CH2:14][CH3:15])[C:7]1=[O:13])(=[O:19])[CH3:33]Participants
5
Procedure
To a solution of 2.5 g of (4-allylthio-3-ethylazetidin-2-on-1-yl)acetic acid in 8 ml of dimethylacetamide was added 0.636 g of freshly ground sodium carbonate. After stirring for 20 minutes, 2.591 g of 4-nitrobenzyl bromide were added in one batch. After about 45 minutes, when the starting material had been consumed, the solution was poured into water and extracted three times with ethyl acetate. The combined organic extracts were washed with saturated sodium bicarbonate, water and saturated brine, and then dried over magnesium sulphate, evaporated in vacuo and chromatographed on silica gel, eluting with ethyl acetate/hexane mixtures to give the title compound as a pale yellow oil. (Yield 3.08 g)
Workup
- waitAfter about 45 minutes
- customwhen the starting material had been consumed
- additionthe solution was poured into water
- extractionextracted three times with ethyl acetate
- washThe combined organic extracts were washed with saturated sodium bicarbonate, water and saturated brine
- dry with materialdried over magnesium sulphate
- customevaporated in vacuo
- customchromatographed on silica gel
- washeluting with ethyl acetate/hexane
Sources & evidence
- ORD record
- ord-180419c568d742588b9ff590192f686d
- Source dataset
- uspto-grants-1984_10
- Patent number
- US04474793
Reaction notes
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