Benzaldehyde → HCID 178496722, compound

Participants

Reaction Steps

To a solution of 50 mg (53 μmol) 16-({[5-(aminomethyl)-4-hydroxy-3-methoxytetrahydro-2-furanyl]oxy}{5-[2,4-dioxo-3,4-dihydro-1 (2H)-pyrimidinyl]-3,4-dihydroxytetrahydro-2-furanyl}methyl)-9-(1-hydroxy-2-methylpropyl)-6-(2-iminohexahydro-4-pyrimidinyl)-2-isopropyl-4,7,10-trioxo-3,5,8,11,15-pentaazaheptadecane-1,17-dioic acid (λmax nm in water=259) in 0.4 ml of methanol is added 11 mg (2.0 eq., 106 μmol) of benzaldehyde and 3.3 mg (1.0 eq., 53 μmol) of NaBH3CN. After stirring for 5 minutes, 0.04 ml of methanolic hydrochloric acid is added. The reaction mixture is then stirred for 0.5 hour. The reaction is monitored by MS. The solvent is removed under reduced pressure to give a yellow gum. The desired products are separated by preparative HPLC to give 15 mg (26% yield) of Example 20a as a white solid and 2.5 mg (4% yield) of Example 20b as a white solid.

Provenance & Evidence