Reaction equation
[CH:1]1([NH:4][C:5]([CH:7]2[CH:9]([CH2:10][CH2:11][CH3:12])[O:8]2)=[O:6])[CH2:3][CH2:2]1.[N-:13]=[N+:14]=[N-:15].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>CO>[N:13]([CH:9]([CH2:10][CH2:11][CH3:12])[CH:7]([OH:8])[C:5]([NH:4][CH:1]1[CH2:3][CH2:2]1)=[O:6])=[N+:14]=[N-:15]Participants
5
Conditions
- Temperature
- 65 °C
Procedure
A flask equipped with an overhead stirrer, thermometer and reflux condenser was placed under a nitrogen atmosphere then charged with the epoxide of Example 5 (20.0 g, 118 mmol), sodium azide (NaN3; 31.0 g, 473 mmol), magnesium sulfate (MgSO4; 14.0 g, 118 mmol) and methanol (MeOH; 200 mL). The mixture was heated to 65±5° C. for 2 hours then cooled to 25±5° C. and filtered through a pad of Celite 545. The solvent was removed under reduced pressure resulting in a thick oil which was taken up in IPAc (250 mL) then washed with water (3×250 mL). The organic phase was dried over sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure to provide the title compound (15.1 g, 60%) as a white solid.
Workup
- customA flask equipped with an overhead stirrer
- temperaturethermometer and reflux condenser
- temperaturethen cooled to 25±5° C.
- filtrationfiltered through a pad of Celite 545
- customThe solvent was removed under reduced pressure
- customresulting in a thick oil which
- washthen washed with water (3×250 mL)
- dry with materialThe organic phase was dried over sodium sulfate (Na2SO4)
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-25a5dc2e49b3415da27073e18cb56a84
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08383858B2
Linked notes
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