Water → (3R,4R)-3-benzyloxycarbonylamino-4-(2-oxoethyl)azetidin-2-one
Reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]1[C@@H:15]([CH2:16][CH:17](OC)[O:18]C)[NH:14][C:13]1=[O:22])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CSC.O>C(O)(=O)C>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]1[C@@H:15]([CH2:16][CH:17]=[O:18])[NH:14][C:13]1=[O:22])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
5
Conditions
- Temperature
- 50 °C
Procedure
To a solution of (3R,4R)-3-benzyloxycarbonylamino-4-(2,2-dimethoxyethyl)azetidin-2-one (2.15 g) in acetic acid (35.2 ml) were added dimethylsulfide (2 ml) and water (8.8 ml) at ambient temperature and the mixture was heated at 50° C. for 4.5 hours. The reaction mixture was evaporated in vacuo and the residue was dissolved in xylene (40 ml). The mixture was evaporated in vacuo and the residue was chromatographed on silica gel (10 g) eluting with a mixture of methylene chloride and acetone (5:1-2:1) to give a crystalline solid. This crude crystals were washed with ether and dried over phosphorous pentoxide to give (3R,4R)-3-benzyloxycarbonylamino-4-(2-oxoethyl)azetidin-2-one (863 mg).
Workup
- customThe reaction mixture was evaporated in vacuo
- dissolutionthe residue was dissolved in xylene (40 ml)
- customThe mixture was evaporated in vacuo
- customthe residue was chromatographed on silica gel (10 g)
- washeluting with a mixture of methylene chloride and acetone (5:1-2:1)
- customto give a crystalline solid
- washThis crude crystals were washed with ether
- dry with materialdried over phosphorous pentoxide
Sources & evidence
- ORD record
- ord-183059f7a92449f0838b97f01a873fdb
- Source dataset
- uspto-grants-1985_09
- Patent number
- US04539152
Reaction notes
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