Chloroacetamide → N-[N2-(1(S)-carboxy-3-phenylpropyl)-N6-carbamoylmethyl-L-lysyl]-L-proline

Participants

Reaction Steps

In 4.0 ml of water there was dissolved N-[N2 -(1(S)-carboxy-3-phenylpropyl)-L-lysyl]-L-proline (406 mg, 0.0001 mole), after which triethylamine (364 mg, 0.0036 mole) was added, followed by slow, dropwise addition of a solution of 2-chloroacetamide (140.3 mg, 0.0015 mole) in 6.0 ml of ethanol. The reaction mixture was stirred at room temperature for 15 minutes, followed by refluxing with stirring for 15 hours. Thin layer chromatography indicated a nearly complete reaction, and the refluxing was continued for 2 more hours. The reaction mixture is allowed to cool and then concentrated under vacuum, flushed with benzene 3 times, then further concentrated under vacuum. The crude product was purified on a 2.5×240 cm LH-20 chromatographic column using a methanol system. Product-rich fractions were evaporated to dryness and freeze-dried to give N-[N2 -(1(S)-carboxy-3-phenylpropyl)-N6 -carbamoylmethyl-L-lysyl]-L-proline.

Provenance & Evidence