Triethylamine → HCID 70072902, compound

Participants

Reaction Steps

3.34 g (10 mmol) of ethoxycarbonyl-3-phenyl-D-alanine hydroxysuccinimidate (Synthesis 1, Step B) is dissolved in 15 ml of pyridine and 1.15 g (10 mmol) of L-proline and 1.4 ml (10 mmol) of triethylamine are added. The reaction mixture is stirred at room temperature for 10 hours, then evaporated at a pressure of 2.0-2.5 kPa. The residue is distributed between 30 ml 5% NaHCO3 solution and 10 ml of diethyl ether. The aqueous phase is washed with 3×5 ml of diethyl ether, the pooled organic washings are extracted with 5 ml 5% NaHCO3-solution. The bicarbonate phases are pooled, acidified with 1M KHSO4 solution to pH3 and extracted with 3×10 ml of ethyl acetate. The pooled organic extracts are dried over anhydrous sodium sulphate and evaporated at a pressure of 2.0-2.5 kPa. The oily residue is crystallised with diethyl ether, the crystals are filtered, washed with diethyl ether and dried in a vacuum desiccator.

Provenance & Evidence