Isopropanol → [(2R,3R)-3-{1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-4-oxoazetidin-2-yl]acetic acid
Reaction equation
CC1(C)[O:9][CH2:8][CH2:7][C@H:6]2[N:3]1[C:4](=[O:27])[C@H:5]2[C:10]([CH3:26])([O:12][C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=1)=[O:14])[CH3:11].CC(C)=[O:31].OS(O)(=O)=O.O=[Cr](=O)=O.C(O)(C)C>CC(C)=O>[CH3:26][C:10]([C@@H:5]1[C:4](=[O:27])[NH:3][C@@H:6]1[CH2:7][C:8]([OH:31])=[O:9])([O:12][C:13]([O:15][CH2:16][C:17]1[CH:18]=[CH:19][C:20]([N+:23]([O-:25])=[O:24])=[CH:21][CH:22]=1)=[O:14])[CH3:11]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of (6R,7R)-2,2-dimethyl-7-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-1-aza-3-oxabicyclo[4.2.0]octan-8-one (11.99 g) in acetone (119.9 ml) was added dropwise to a solution of 2N Jones reagent (38.13 ml) in acetone (119.9 ml) at ambient temperature over a period of an hour, and the mixture was stirred for an additional 30 minutes. After addition of an excess of isopropyl alcohol to the mixture, the solvent was removed by evaporation. The residue was dissolved in ethyl acetate (1 l) and the solution was washed with water. The aqueous washings were extracted with ethyl acetate (200 ml). The organic layers were combined, washed with an aqueous sodium chloride, dried over magnesium sulfate, and evaporated to give 2-[(2R,3R)-3-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-4-oxo-azetidin-2-yl]acetic acid (11.8 g).
Workup
- customthe solvent was removed by evaporation
- dissolutionThe residue was dissolved in ethyl acetate (1 l)
- washthe solution was washed with water
- extractionThe aqueous washings were extracted with ethyl acetate (200 ml)
- washwashed with an aqueous sodium chloride
- dry with materialdried over magnesium sulfate
- customevaporated
Sources & evidence
- ORD record
- ord-9cae4d74bbee404180542a14dfce17d1
- Source dataset
- uspto-grants-1987_02
- Patent number
- US04640915
Reaction notes
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