3-[methyl(pentyl)amino]propanoic acid

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 68.8 g (367.4 mmol) N-methyl-N-pentyl-β-alanine methyl ester was hydrolyzed by refluxing with 138 ml water. Water was distilled off and 300 ml diethyl carbonate were added, followed by azeotropic distillation of diethyl carbonate/water (30 ml) to remove residual water. About 290 ml of a diethyl carbonate solution containing 63 g N-methyl-N-pentyl-β-alanine was obtained which could directly be used for the subsequent bisphosphorylation step. Water was distilled off 300 ml diethyl carbonate were added followed by azeotropic distillation of diethyl carbonate/water (30 ml) to remove residual water About 290 ml of a diethyl carbonate solution containing 63 g N-methyl-N-pentyl-β-alanine was obtained which

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The hydrolysis can be performed by refluxing the N-methyl-N-pentyl-β-alanine methyl ester in a diluted mineral acid, but can also be performed by refluxing in water at least until no ester can be detected any further. Formation of the hydrohalogenide such as the hydrobromide or the hydrochloride, preferably of the hydrochloride (X═Cl) can be effected by addition of an aqueous solution of the appropriate mineral acid. The resulting N-methyl-N-pentyl-β-alanine hydrohalogenide, e.g., hydrochloride, can be isolated by distilling of the water and by a crystallization of the residue in a suitable solvent such as toluene/acetone or methyl ethyl ketone, preferably in methyl ethyl ketone. The hydrolysis