(3R,4R)-4-(2,2-dimethoxyethyl)-3-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-azetidin-2-one → (3R,4R)-3-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-4-(2-oxoethyl)azetidin-2-one
Reaction equation
C[O:2][CH:3](OC)[CH2:4][C@H:5]1[NH:8][C:7](=[O:9])[C@H:6]1[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]>C(O)(=O)C>[CH3:26][C:10]([C@H:6]1[C@@H:5]([CH2:4][CH:3]=[O:2])[NH:8][C:7]1=[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
3
Procedure
A solution of (3R,4R)-4-(2,2-dimethoxyethyl)-3-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-azetidin-2-one (64 mg) in 80% aqueous acetic acid (3.0 ml) was heated at 50°-55° C. for 4 hours. After evaporation of the solvent, the residue was dissolved in ethyl acetate (20 ml) and the solution was washed with aqueous sodium bicarbonate. The aqueous layer was extracted with ethyl acetate (10 ml). The organic layers were combined, washed with water and brine, dried over magnesium sulfate and evaporated in vacuo to give (3R,4R)-3-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-4-(2-oxoethyl)-azetidin-2-one (55 mg) as a solid.
Workup
- customAfter evaporation of the solvent
- dissolutionthe residue was dissolved in ethyl acetate (20 ml)
- washthe solution was washed with aqueous sodium bicarbonate
- extractionThe aqueous layer was extracted with ethyl acetate (10 ml)
- washwashed with water and brine
- dry with materialdried over magnesium sulfate
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-f32faa02d16649089e9b62e6f45c3a6f
- Source dataset
- uspto-grants-1985_09
- Patent number
- US04539152
Reaction notes
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