Sodium Iodide → tert-Butyl(2R)-2-(3-azido-2-oxopyrrolidin-1-yl)propanoate
Reaction equation
[C:1]([O:5][C:6](=[O:10])[C@@H:7]([CH3:9])[NH2:8])([CH3:4])([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C.[N:20]([CH:23]([CH2:29][CH2:30]Br)[C:24](OCC)=[O:25])=[N+:21]=[N-:22].[I-].[Na+]>C(#N)C>[N:20]([CH:23]1[CH2:29][CH2:30][N:8]([C@H:7]([CH3:9])[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:10])[C:24]1=[O:25])=[N+:21]=[N-:22]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a solution of D-alanine tert-butylester (1.28 g) and N,N-diisopropylethylamine (1.22 ml) in acetonitrile (15 ml), was added a solution of ethyl 2-azido-4-bromobutanoate (1 g) and sodium iodide (0.02 g) in acetonitrile (5 ml). The mixture was heated at 60° C. for 60 h and then concentrated under reduced pressure to give a brown oil. This oil was partitioned between DCM and water. The separated organic layer was washed further with water and dried (over magnesium sulphate), and concentrated under reduced pressure. The residual brown oil was purified using Biotage™ chromatography (silica, eluting with cyclohexane:ethyl acetate 3:1) to give the title compound (0.204 g) as a mixture of two diastereoisomers.
Workup
- concentrationconcentrated under reduced pressure
- customto give a brown oil
- customThis oil was partitioned between DCM and water
- washThe separated organic layer was washed further with water
- dry with materialdried (over magnesium sulphate)
- concentrationconcentrated under reduced pressure
- customThe residual brown oil was purified
- washBiotage™ chromatography (silica, eluting with cyclohexane:ethyl acetate 3:1)
Sources & evidence
- ORD record
- ord-3d62b2ef92aa44b5aebc5bf1cf9b9b78
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07429587B2
Reaction notes
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