Oxalic Acid → HCID 15297816, compound

Participants

Reaction Steps

(2S)-1-(N-Benzyloxycarbonyl-L-prolyl)-2-[1-hydroxy-2-(phenylthio)ethyl]pyrrolidine (908 mg) was dissolved in DMSO (3 ml) and benzene (3 ml), and thereto were added pyridine (162 μl), trifluoroacetic acid (78 μl) and DCC (1.24 g) in order, and the mixture was stirred at room temperature for 1 hour. Ethyl acetate (50 ml) was added to the reaction mixture, and oxalic acid (540 mg) in methanol (5 ml) was added thereto, followed by stirring for 30 minutes. Water (50 ml) was added to the reaction mixture and the resultant dicyclohexylurea was filtered off. The filtrate was washed with 1N hydrochloric acid, a saturated aqueous solution of sodium bicarbonate and saturated brine in order, and dried over magnesium sulfate, followed by concentration. The residue was purified by silica gel column chromatography (eluate: chloroform-methanol) to give 714 mg of (2S)-1-(N-benzyloxycarbonyl-L-prolyl)-2-[(Phenylthio) acetyl]pyrrolidine (See Table 1).

Provenance & Evidence