benzyl 3-aminopropanoate;hydrochloride

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

Procedure: Compound (25) (517 mg, 1.85 mmol) was treated with 4N HCl in dioxane at room temperature for 2 h. The reaction mixture was evaporated at reduced pressure, evaporated from toluene and then dried under vacuum to give crude benzyl β-alaninate hydrochloride which was used without further purification. The reaction mixture was evaporated at reduced pressure evaporated from toluene dried under vacuum

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

Procedure: To an ice bath cooled solution of benzyl 3-aminopropanoate hydrochloride (4.49 g, 20.8 mmol) in DMF (30 mL) was added K2CO3 (3.02 g, 21.84 mmol) and the resulting mixture was stirred at o° C. for 2 hr. The mixture was then filtered and the filtrate was added to an ice bath cooled solution of 2-(2,6-dioxomorpholino)acetic acid (4.47 g, 25.8 mmol) in DMF (30 mL). The resulting mixture was stirred at 0° C. for 30 min, then at rt for 2 hr. The reaction was quenched by the addition of water (30 mL) and the resulting mixture was concentrated. The residue was stirred with water (40 mL), and the resulting precipitate was collected through filtration and dried to give the title compound. 1H NMR (DMSO-d6) δ 2.53 (t, J=6.8, 2H), 3.27 (s, 2H), 3.36 (q, J=6.2, 2H), 3.42 (m, m 2H), 3.49 (s, 2H), 5.09 (s, 2H), 7.28 (m, 4H), 8.16 (m, 1H), 12.45 (br s, 2H). The mixture was then filtered the filtrate was added to an ice bath The resulting mixture was stirred at 0° C. for 30 min at rt for 2 hr The reaction was quenched by the addition of water (30 mL) the resulting mixture was concentrated The residue was stirred with water (40 mL) the resulting precipitate was collected through filtration dried