Isopropanol → 2-[(2R, 3S)-3-(1-methoxy-1-methylethyl)-4-oxoazetidin-2-yl]acetic acid
Reaction equation
[OH:1][CH2:2][CH2:3][C@H:4]1[NH:7][C:6](=[O:8])[C@@H:5]1[C:9]([O:12][CH3:13])([CH3:11])[CH3:10].CC(C)=[O:16].OS(O)(=O)=O.O=[Cr](=O)=O.C(O)(C)C>CC(C)=O>[CH3:13][O:12][C:9]([C@H:5]1[C:6](=[O:8])[NH:7][C@@H:4]1[CH2:3][C:2]([OH:16])=[O:1])([CH3:11])[CH3:10]Participants
Procedure
A solution of (3S, 4R)-4-(2-hydroxyethyl)-3-(1-methoxy-1-methylethyl)azetidin-2-one (50.7 mg) in acetone (5.42 ml) was added to a solution of 2N Jones reagent (0.542 ml) in acetone (5.42 ml) at ambient temperature over a period of 30 minutes, and the mixture was stirred for an hour. After addition of an excess of isopropyl alcohol to the mixture, the solvent was removed. The residue was dissolved in chloroform and the resultant solution was washed with a saturated aqueous sodium chloride. The washings were extracted five times with chloroform. The extracts were combined, dried over magnesium sulfate, filtered and evaporated. The crystalline residue was washed with isopropyl alcohol to give 2-[(2R, 3S)-3-(1-methoxy-1-methylethyl)-4-oxoazetidin-2-yl]acetic acid (25.1 mg). The mother liquor was concentrated and the crystalline residue was washed with hexane to give a second crop of the above product (19.4 mg). Total yield is 44.5 mg.
Workup
- customthe solvent was removed
- dissolutionThe residue was dissolved in chloroform
- washthe resultant solution was washed with a saturated aqueous sodium chloride
- extractionThe washings were extracted five times with chloroform
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- customevaporated
- washThe crystalline residue was washed with isopropyl alcohol
Sources & evidence
- ORD record
- ord-80547e644c0d49b3bc4480657a38ecef
- Source dataset
- uspto-grants-1987_02
- Patent number
- US04640915
Reaction notes
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