Sodium Methoxide → HCID 70447142, compound
Reaction equation
[CH3:1][C:2]([CH3:21])=[C:3]([N:8]1[C@H:11]([CH2:12][CH:13]=[CH2:14])[C@@H:10]([C@H:15]([O:17]C=O)[CH3:16])[C:9]1=[O:20])[C:4]([O:6][CH3:7])=[O:5].C[O-].[Na+]>CO.C(O)(=O)C>[CH3:21][C:2]([CH3:1])=[C:3]([N:8]1[C@H:11]([CH2:12][CH:13]=[CH2:14])[C@@H:10]([C@H:15]([OH:17])[CH3:16])[C:9]1=[O:20])[C:4]([O:6][CH3:7])=[O:5]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
Methyl 3-methyl-2-[(3S,4R)-3-[(1R)-1-formyloxyethyl]-2-oxo-4-allylazetidin-1-yl]but-2-enoate (23 mg) was dissolved in methanol (1 ml) and cooled to 0° C. To this solution was added a solution of sodium methoxide in methanol (0.49 M, 0.16 ml) and the mixture was stirred for 1 hour at the same temperature. An additional 0.08 ml of the sodium methoxide solution was added and the mixture was stirred for 30 minutes at the same temperature. Acetic acid (2 drops) was then added and the mixture was evaporated. The residue was dissolved in ethyl acetate, washed with aqueous sodium bicarbonate and brine, dried over magnesium sulfate and evaporated. The residue was purified by preparative thin layer chromatography (silica gel) developing with methylene chloride and ethyl acetate (2:1) to give methyl 3-methyl-2-[(3S,4R)-3-((1R)-1-hyroxyethyl)-2-oxo-4-allylazetidin-1-yl]but-2-enoate (20 mg).
Workup
- stirringthe mixture was stirred for 30 minutes at the same temperature
- customthe mixture was evaporated
- dissolutionThe residue was dissolved in ethyl acetate
- washwashed with aqueous sodium bicarbonate and brine
- dry with materialdried over magnesium sulfate
- customevaporated
- customThe residue was purified by preparative thin layer chromatography (silica gel)
Sources & evidence
- ORD record
- ord-cf1c928f22bb419cb69443de4ac7287f
- Source dataset
- uspto-grants-1983_05
- Patent number
- US04383945
Reaction notes
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