N,N-Dimethyl-1,3-propanediamine → methyl 2-[(4R)-3-amino-4-allyl-2-oxoazetidin-1-yl]-3-methyl-2-butenoate
Reaction equation
[CH2:1]([C@H:4]1[N:7]([C:8](=[C:13]([CH3:15])[CH3:14])[C:9]([O:11][CH3:12])=[O:10])[C:6](=[O:16])[C@@H:5]1[N:17]1C(=O)C2=CC=CC=C2C1=O)[CH:2]=[CH2:3].CN(C)CCCN>C(Cl)Cl.CO>[NH2:17][CH:5]1[C@@H:4]([CH2:1][CH:2]=[CH2:3])[N:7]([C:8](=[C:13]([CH3:15])[CH3:14])[C:9]([O:11][CH3:12])=[O:10])[C:6]1=[O:16]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of methyl 2-[(3R,4R)-4-allyl-3-phthalimido-2-oxoazetidin-1-yl]-3-methyl-2-butenoate (2.64 g) in a mixture of methylene chloride (20 ml) and methanol (10 ml) was added N,N-dimethyl-1,3-propanediamine (1.98 ml) and the mixture was left in a refrigerator for 3 days and at room temperature for 24 hours. The reaction mixture was evaporated and the residue was dissolved in ethyl acetate (50 ml), washed with water, dried over magnesium sulfate and evaporated to give an oil, which was chromatographed on silica gel eluting with a mixture of methylene chloride and acetone (6-5:1) to give methyl 2-[(4R)-3-amino-4-allyl-2-oxoazetidin-1-yl]-3-methyl-2-butenoate (873 mg) as an oil.
Workup
- customThe reaction mixture was evaporated
- dissolutionthe residue was dissolved in ethyl acetate (50 ml)
- washwashed with water
- dry with materialdried over magnesium sulfate
- customevaporated
- customto give an oil, which
- customwas chromatographed on silica gel eluting with a mixture of methylene chloride and acetone (6-5:1)
Sources & evidence
- ORD record
- ord-dcc0817a4ca54980a05453ac391f210d
- Source dataset
- uspto-grants-1985_09
- Patent number
- US04539152
Reaction notes
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