Sodium Hydroxide → O-Methyl-L-Tyrosine

Participants

Reaction Steps

A solution of hydrochloride dihydrate of FR-48736 substance [1-(6-amino-9H-purin-9-yl)-1,3-dideoxy-3-(O-methyl-L-tyrosylamino)-β-D-ribofuranuronic acid hydrochloride dihydrate] (100 mg) prepared by Example 98 in 1N-methanolic sodium hydroxide (10 ml) was refluxed for 20 hours. To the cooled solution was added water (50 ml) and the methanol in the solution was evaporated under reduced pressure. The resulting aqueous solution was adjusted to pH 7 with 1N-hydrochloric acid and applied to a column of activated charcoal (20 ml). The column was washed with water (40 ml) and eluted with a mixture of methanol and water (1:1) (60 ml). The solvent was evaporated under reduced pressure. The residue was chromatographed on a cellulose column and eluted with a mixture of acetonitrile and water (8:2). The first ninhydrin positive and weak UV absorbing fraction was evaporated under reduced pressure to give a powder of O-methyltyrosine (21 mg).

Provenance & Evidence