Reaction equation
[NH2:1][C@H:2]1[C@H:5]([CH3:6])[N:4]([O:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:3]1=[O:15].C1(C)C(S([O-])(=O)=O)=CC=CC=1.[CH3:27][O:28][C:29]1[CH:37]=[CH:36][CH:35]=[C:34]([O:38][CH3:39])[C:30]=1[C:31](Cl)=[O:32]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:39][O:38][C:34]1[CH:35]=[CH:36][CH:37]=[C:29]([O:28][CH3:27])[C:30]=1[C:31]([NH:1][C@H:2]1[C@H:5]([CH3:6])[N:4]([O:7][CH2:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:3]1=[O:15])=[O:32]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a cold (-10° C.) solution of (3S-trans)-3-amino-4-methyl-1-(phenylmethoxy)-2-azetidinone, toluenesulfonate (0.95 g; see example 2D) in methylene chloride (50 ml) is added 2,6-dimethoxybenzoyl chloride (0.60 g) and 4-dimethylaminopyridine (0.61 g). The reaction is stirred under nitrogen and allowed to rise to 26° C. over five hours. The reaction mixture is concentrated to an oil and partitioned between ethyl acetate and aqueous hydrogen sulfate solution. The organic layer is washed with aqueous sodium bicarbonate, and brine, dried over sodium sulfate and concentrated to a foam (0.848 g).
Workup
- concentrationThe reaction mixture is concentrated to an oil
- custompartitioned between ethyl acetate and aqueous hydrogen sulfate solution
- washThe organic layer is washed with aqueous sodium bicarbonate, and brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated to a foam (0.848 g)
Sources & evidence
- ORD record
- ord-b3c4aefaa8124d5eaa3567e0899a03f9
- Source dataset
- uspto-grants-1985_08
- Patent number
- US04533660
Linked notes
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