Cesium carbonate → 2-(((Tert-butoxy)carbonyl)amino)-4-hydroxybutanoic acid

HRID 1371239Notes

Reaction equation

HRID 1371239 reaction equation
[NH2:1][C@H:2]([C:6]([OH:8])=[O:7])[CH2:3][CH2:4][OH:5].C(=O)([O-])[O-].[Cs+].[Cs+].O1CCOCC1.[C:21](OC([O-])=O)(=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24]>O.[OH-].[Na+]>[C:23]([O:22][C:21]([NH:1][CH:2]([C:6]([OH:8])=[O:7])[CH2:3][CH2:4][OH:5])=[O:27])([CH3:26])([CH3:25])[CH3:24]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 12647L-HomoserineHCID 312751,4-DioxaneHCID 22064466Tert-butyldicarbonate

Product 1

HCID 41186272-(((Tert-butoxy)carbonyl)amino)-4-hydroxybutanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

2 g of homoserine (16.78 mmol) were dissolved in 20 ml of water and to the solution 16.78 ml of 1 M NaOH and 3.006 g of cesium carbonate (9.23 mmol) were added. After stirring for 5 minutes, the solution was cooled in an ice/water bath. 60 ml of dioxane and terbutyl 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 removed under vacuum. The dry residue was directly used in the next step.

Workup

  1. additionwere added
  2. temperaturethe solution was cooled in an ice/water bath
  3. stirringunder stirring in an ice-cold water bath for 1 hour
  4. waitat room temperature for 5 hours
  5. customThe solvent was subsequently removed under vacuum

Sources & evidence

ORD record
ord-cf4616811569449692461c6364a80d67
Source dataset
uspto-grants-2007_01
Patent number
US07157092B1

Reaction notes

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