triethylamine in N,N-dimethyl-formamide T=60°C; Condensation; 16 h;

1.1: NaOH / H2O; methanol; toluene 1.2: 55 percent / POCl3 / toluene / 2 h / 100 °C 2.1: 90 percent / NaBH4 / methanol / 2 h / 20 °C View Scheme

1: glycine With sodium hydroxide in methanol T=0°C; 0.25 h; 2: methyl pentanimidate in methanol T=0 - 20°C; 16.16 - 16.25 h; 3: N,N-dimethyl-formamide With sodium hydroxide; water; trichlorophosphate; copper(II) bis(trifluoromethanesulfonate) Product distribution / selectivity; more than 3 stages;

1: aq. KOH / toluene; methanol / 15 h / 40 °C 2: 132 g / POCl3 / toluene / 3 h / 97 - 100 °C View Scheme

1: 93 percent / triethylamine / dimethylformamide / 16 h / 60 °C View Scheme

1: 95 percent / NaOH / methanol; toluene / 3 h / 20 °C 2: 31 percent / POCl3 / chlorobenzene / 2 h / 100 °C View Scheme

1: triethylamine / dimethylformamide / 16 h / 60 °C 2: 83 percent / potassium carbonate / CHCl3; H2O / 8 h / Heating View Scheme

1: With hydrogenchloride T=-10 - 15°C; P=1103.36 - 1471.14 Torr; 30 - 33 h; 2: With ammonia in methanol T=20 - 30°C; pH=8 - 9; 3 h;

1.1: NaOH / H2O; methanol; toluene 1.2: 55 percent / POCl3 / toluene / 2 h / 100 °C 2.1: 90 percent / NaBH4 / methanol / 2 h / 20 °C 3.1: NaOMe / dimethylformamide / 0.5 h / 25 °C 3.2: 40 percent / dimethylformamide / 24 h / 20 °C View Scheme