Hydrochloric Acid → HCID 135407359, compound

Participants

Reaction Steps

Anhydrous methanol (1 ml) was added to 2-amino-9-[(1S,3S,4S)-3,4-bis(benzoyloxymethyl)-cyclohexyl]-6-(2-methoxyethoxy)-purine (17.4 mg, 0.03 mmole). While cooling the mixture with ice, sodium methoxide (1.62 mg, 0.03 mmole) was added thereto, and the whole mixture was stirred at room temperature overnight. The reaction mixture was neutralized with dilute hydrochloric acid, and the solvent was distilled off under reduced pressure. Then, ethyl ether and water were added to the mixture, an ethyl ether layer was removed, and water was distilled off. The residue was heated at 100° C. for one hour together with 2N aqueous hydrochloric acid (1 ml). After neutralizing the reaction mixture with 1N solution of sodium hydroxide, the reaction mixture was subjected to Diaion HP-20 column chromatography (methanol concentration gradient) to obtain 9-[(1S,3S,4S)-3,4-bis(hydroxymethyl)cyclohexyl]-guanine (5.7 mg, 31.3%).

Provenance & Evidence