Chloroacetamide → N-(Carbamoylmethyl)-beta-alanine ethylester

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

A suspension of 2-chloroacetamide (2.34 g, 25.0 mmol), β-alanine ethyl ester hydrochloride (15.36 g, 100 mmol) and K2CO3 (42.0 g) in dry DMF (200 mL) was heated at 90° C. for 24 hours. After cooling to room temperature the reaction mixture was filtered to remove any unreacted β-alanine ethyl ester and the solvent and was removed by distillation under reduced pressure (50° C., 1 Torr). The resulting yellow oil (6.0 g) was purified by silica gel flash column chromatography using ethyl acetate, ethyl acetate/ethanol (2:1, v/v), and finally ethanol as the eluent, to give 2.24 g (50%) of the title compound as a colorless oil. TLC (methanol, det. ninhydrin, Rf=0.65). 1H NMR (DMSO-d6) δ1.18 (t, J=7.1 Hz, 3H, CH3), 2.42, 2.70 (2t, J=6.7 Hz, 4H, CH2CH2), 3.03 (s, 2H, CH2), 4.06 (q, J=7.1 Hz, 2H, OCH2), 7.02, 7.24 (2s (br), 2H, NH2) ppm. 13C NMR (DMSO) δ14.1 (CH3), 34.5 (CH2CO), 44.7 (NCH2CH2), 51.8 (NCH2CN), 59.8 (OCH2), 172.1 (C═O), 173.5 (C═O) ppm. FAB-MS: m/z 175.1 (M+1)+.

Herkunft & Nachweise