Tert-butyl 2-[4-[3-[(4-amino-2,6-dioxo-1,3-dipropylpyrimidin-5-yl)amino]-2-methyl-3-oxopropyl]phenoxy]acetate → (+)-2-[4-[2-(2,3,6,9-tetrahydro-1,3-dipropyl-2,6-dioxo-1H-purin-8-yl)propyl]phenoxy]acetic acid, ethyl ester

Participants

Reaction Conditions

Reaction Steps

Dissolve the ethyl enolate of (-)-2-[[4-[3-[(6-amino-1-propyl-1,2,3,4-tetrahydro-3-propyl-2,4-dioxo-5-pyrimidinyl)amino]-2-methyl-3-oxopropyl]phenyl]oxy]-acetic acid, 1,1-dimethylethyl ester (1.01 g, 1.9 mmol) in anhydrous benzene (200 mL) and heat at 80° C. for 24 hours. Evaporate the solvent in vacuo and purify the residue by radial chromatography (40→50% ethyl acetate/hexane) to give (-)-2-[4-[2-(2,3,6,9-tetrahydro-1,3-dipropyl-2,6-dioxo-1H-purin-8- yl)propyl]phenoxy]acetic acid, ethyl ester (0.7 g, 81%); [α]d 20 =-54.3° (C=0.856, CHCl3).

Provenance & Evidence