benzyl 3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate

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: N-t-Butyloxycarbonyl-β-alanine (2.0 g, 10.6 mmol) in methylene chloride (50 mL) was treated with benzyl alcohol (1.66 mL, 26.0 mmol), N,N-dicyclohexylcarbodiimide (2.39 g, 11.6 mmol) and N,N-dimethylaminopyridine (1.42 g, 11.6 mmol) and the subsequent reaction mixture was stirred at room temperature for 54 h. The reaction mixture was filtered and evaporated at reduced pressure. The residue was purified using flash chromatography (silica gel, 50% ethyl acetate/hexane) to yield the title compound (25) (2.43 g, 82%). 1H NMR (CDCl3) ε 1.47 (s, 9H), 2.61 (t, 2H, J=6 Hz), 3.45 (q, 2H, J=7.5 Hz), 5.15 (br s, 1H), 5.27 (s, 2H), 7.43 (s, 5H). The reaction mixture was filtered evaporated at reduced pressure The residue was purified