[2-adenin-9-yl-5-[[[[5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-oxido-phosphoryl]oxy-oxido-phosphoryl]oxymethyl]-4-hydroxy-tetrahydrofuran-3-yl] phosphate → 8-[4-(4-Nitro-2-sulfobenzamido)-2-sulfobenzamido]-1,3,6-naphthalenetrisulfonic acid

Participants

Reaction Steps

To an ice-cold solution of 17.2 g of 8-(4-amino-2-sulfobenzamido)-1,3,6-naphthalenetrisulfonic acid, tetrasodium salt, and 5.24 g of sodium acetate trihydrate in 100 ml of water was added 6.87 g of 4-nitro-2-sulfobenzoic anhydride. The mixture was stirred for 10 minutes, and filtered through diatomaceous earth. The filtrate was poured into 750 ml of absolute ethanol with vigorous stirring and cooled in an ice bath. The solid was recovered by filtration, washed with ethanol and ether and evaporated in vacuo overnight. This solid was dissolved in 100 ml of water, acidified with 3 ml of concentrated hydrochloric acid, and then poured with vigorous stirring into 500 ml of cold absolute ethanol. The solid was collected by filtration, washed with ethanol, then ether, and dried overnight at 110° C., giving 19.35 g of 8-[4-(4-nitro-2-sulfobenzamido)-2-sulfobenzamido]-1,3,6-naphthalenetrisulfonic acid, pentasodium salt as a powder.

Provenance & Evidence