Beta-Alanine → Sodium butyl glycidyl phosphate
Reaction equation
N[CH2:2][CH2:3][C:4](O)=O.O.[P:8]([O-:17])([O-:16])([O:10][CH2:11][CH:12]([OH:15])[CH2:13]Cl)=[O:9].[Na+:18].[Na+].[OH-].[Na+].[CH2:22](O)C>>[P:8]([O-:17])([O:10][CH2:11][CH:12]1[O:15][CH2:13]1)([O:16][CH2:4][CH2:3][CH2:2][CH3:22])=[O:9].[Na+:18]Participants
Conditions
- Temperature
- 70 °C
Procedure
β-Alanine, 30.0 g (0.337 mol), was charged into a reaction vessel, into which 100 ml of water was added and the mixture was stirred. Its temperature was raised to 70° C. and the mixture was homogenized. Then, while maintaining the temperature, an ethanol solution of 750 g (0.112 mol) of sodium butyl glycidyl phosphate, which was prepared by the reaction of 30.2 g (0.112 mol) of sodium 2-hydroxy-3-chloropropyl phosphate and sodium hydroxide in ethanol, followed by purification by desalting, was added dropwise, and stirring was continued for further 6 hours. The reaction was terminated, when the analysis by HPLC indicated extinction of the peak for the raw material and appearance of the peak for the new product. Upon completion of the reaction, the product was collected by fractionation by HPLC. The solvent was evaporated in vacuo to produce 35.8 g of sodium 2-hydroxy-3-N-carboxyethylammoniopropyl phosphate at a yield of 99.3%.
Workup
- additionwas added
- stirringthe mixture was homogenized
- temperatureThen, while maintaining the temperature
- customfollowed by purification
- additionwas added dropwise
- stirringstirring
- customThe reaction was terminated
- customUpon completion of the reaction
- customthe product was collected by fractionation by HPLC
- customThe solvent was evaporated in vacuo
Sources & evidence
- ORD record
- ord-daabaf86d1eb4c16a1308811fd99ac77
- Source dataset
- uspto-grants-1991_12
- Patent number
- US05071585
Reaction notes
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