Cesium carbonate → 2-(((Tert-butoxy)carbonyl)amino)-4-hydroxybutanoic acid
Reaction equation
[NH2:1][C@H:2]([C:6]([OH:8])=[O:7])[CH2:3][CH2:4][OH:5].[OH-].[Na+].C(=O)([O-])[O-].[Cs+].[Cs+].[C:17](OC([O-])=O)(=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20]>O.O1CCOCC1>[C:19]([O:18][C:17]([NH:1][CH:2]([C:6]([OH:8])=[O:7])[CH2:3][CH2:4][OH:5])=[O:23])([CH3:22])([CH3:21])[CH3:20]Participants
7
Procedure
To a solution of homoserine bromohydrate (2 g; 16.78 mmol.) in H2O (20 ml), addition was made in succession of a 1 M NaOH solution (16.78 ml) and cesium carbonate (3.01 g; 9.23 mmol.). After stirring for 5 minutes, the solution was cooled in an ice/water bath. Dioxane (60 ml) and t-butyl pyrocarbonate were then added. The reaction mixture was kept under stirring in an ice-cold water bath for 1 hour and thereafter at room temperature for 5 hours. The solvent was subsequently evaporated under vacuum and the dry residue was directly used in the next step.
Workup
- temperaturethe solution was cooled in an ice/water bath
- stirringunder stirring in an ice-cold water bath for 1 hour
- waitat room temperature for 5 hours
- customThe solvent was subsequently evaporated under vacuum
Sources & evidence
- ORD record
- ord-68403ee0ef8d4fe796066fad4f53fe74
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08173133B2
Reaction notes
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