Triethylamine → 1-(6-benzoylamino-9H-purin-9-yl)-1,3-dideoxy-3-(N-benzyloxycarbonyl-L-phenylalanylamino)-beta-D-ribofuranuronic acid

Participants

Reaction Steps

To a solution of 1-(6-benzoylamino-9H-purin-9-yl)-1,3-dideoxy-3-amino-β-D-ribofuranuronic acid (384 mg) prepared in Example 1 and triethylamine (0.19 ml) in water (10 ml) was added a solution of N-hydroxysuccinimide ester of N-benzyloxycarbonyl-L-phenylalanine (635 mg) in tetrahydrofuran (10 ml) at room temperature under stirring, which was continued overnight. The mixture was evaporated to remove tetrahydrofuran, acidified with 10% hydrochloric acid and extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate and evaporated to dryness. The residue was triturated in diethyl ether to give 1-(6-benzoylamino-9H-purin-9-yl)-1,3-dideoxy-3-(N-benzyloxycarbonyl-L-phenylalanylamino)-β-D-ribofuranuronic acid (521 mg), mp. 145°-150° C. (dec.).

Provenance & Evidence