Pyridine → HCID 22847765, compound

Participants

Reaction Steps

0.8 g of t-butoxycarbonyl-L-phenylalanine was dissolved in 5 ml of pyridine, treated at -5° with 0.3 ml of oxalyl chloride and stirred at 0-5° for 10 minutes. After the addition of 0.7 g of benzyl-(S)-3-carbamoyl-2-hydroxypropionic acid (which was prepared according to the directions in Agr. Biol. Chem. 40, 1651 (1976) and Int. J. Peptide Protein Res. 20, 35 (1982)) in 1 ml of pyridine, the mixture was stirred at 0°-5° for 2 hours and thereafter at room temperature for 1 hour. The reaction mixture was then poured onto ice and extracted twice with 50 ml of ethyl acetate each time. The combined organic extracts were washed with 50 ml of 3N hydrochloric acid and 50 ml of saturated sodium bicarbonate solution, dried over sodium sulfate and evaporated. The residue was purified by flash chromatography on 50 g of silica gel using a 10:1 mixture of methylene chloride and methanol as the eluting agent to obtain there was obtained 0.9 g of (S)-2-[[N-(t-butoxycarbonyl)-3-phenyl-L-alanyl]oxy]succinamide benzyl ester as a yellow powder. MS: 397 (M--C4H9O)+.

Provenance & Evidence