Glycine → N-carboxymethyl-1-(6-benzoylamino-9H-purin-9-yl)-1,3-dideoxy-3-(N-benzyloxycarbonyl-O-methyl-L-tyrosylamino)-beta-D-ribofuranuronamide

Participants

Reaction Steps

A solution of N-hydroxysuccinimide ester of 1-(6-benzoylamino-9H-purin-9-yl)-1,3-dideoxy-3-(N-benzyloxycarbonyl-O-methyl-L-tyrosylamino)-β-D-ribofuranuronic acid (295 mg) prepared in Example 53 (1) in tetrahydrofuran was added to a solution of glycine (30 mg) and triethylamine (0.085 ml) in water (5 ml). The mixture was stirred for 20 hours at room temperature and concentrated under reduced pressure to remove tetrahydrofuran. The aqueous solution was acidified with 1N hydrochloric acid and extracted with a mixed solvent (chloroform/ethanol=1/1). The extract was dried and evaporated to dryness. The residue was triturated in diethyl ether to give N-carboxymethyl-1-(6-benzoylamino-9H-purin-9-yl)-1,3-dideoxy-3-(N-benzyloxycarbonyl-O-methyl-L-tyrosylamino)-β-D-ribofuranuronamide (244 mg), mp. 122°-130° C. (dec.).

Provenance & Evidence