Dimethylformamide → 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide

Participants

Reaction Steps

N-[(t-Butoxycarbonyl)-L-glutamic acid 1-methylamide 5-benzyl ester [0.55 g, S-isomer of the compound (XV) wherein R3 is methyl group, and n is 1] is dissolved in methylene chloride (8 ml), and thereto is added TFA (4 ml). The mixture is stirred at room temperature for one hour, and the reaction mixture is concentrated to give the de-protected product [0.81 g, stereoisomer of the compound (XIIa) wherein R3 is methyl group, and n is 1] in the form of TFA salt. The TFA salt of the de-protected product thus obtained is dissolved in DMF (3 ml), and to the mixture are added with stirring diisopropylethylamine (0.97 ml), HOBt (0.31 g), a solution of the compound obtained in the above (1) (0.77 g) in DMF (6 ml), and WSC (0.39 g) under ice-cooling, and the mixture is stirred at room temperature for 18.5 hours. The reaction mixture is poured to ice-water (100 ml), and the mixture is extracted three times with ethyl acetate, and the extract is washed with water, dried, and concentrated under reduced pressure. The resulting residue is purified by silica gel medium-pressure liquid chromatography (chloroform:MeOH=100:0→300:1) to give [N-(t-butoxycarbonyl)-S-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-L-cysteinyl]-L-glutamic acid 1-methylamide 5-benzyl ester (0.88 g) as a syrup.

Provenance & Evidence