2-(butanoylamino)acetic acid

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

Procedure: N-Butanoylglycine ethyl ester (16.3 g, 94.16 mmol) was dissolved in aqueous NaOH (1 M, 282 ml, 282 mmol) and then stirred for 15 h at room temperature. Aqueous HCl (12 M, 15.7 ml, 188 mmol) was added to pH=5. The water was then evaporated (in vacuo) and the residue was dissolved in aqueous HCl (1 M, 175 ml) which gave a pH of 1. The solution was saturated with NaCl and extracted with tetrahydrofuran (3×100 ml). The combined organic extracts was dried with Na2SO4 and evaporated in vacuo yielding 13 g (95%) of N-butanoylglycine. 1H NMR (CDCl3), 0.97 (t; J=7.4 Hz; CH3), 1.64-1.74 (m; CH2), 2.27 (t; J=7.5 Hz; CH2), 4.09 (d; J=5.1 Hz; CH2), 6.24 (broad; NH), 8.1 (broad; COOH). The water was then evaporated (in vacuo) the residue was dissolved in aqueous HCl (1 M, 175 ml) which gave a pH of 1 extracted with tetrahydrofuran (3×100 ml) The combined organic extracts was dried with Na2SO4 evaporated in vacuo