Cyclopropanecarbonyl chloride → Cyclopropanecarboxylic acid {(1S,2R,3S,4R)-4-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-amide

Participants

Reaction Steps

A solution of (1S,2R,3S,5R)-3-Amino-5-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-cyclopentane-1,2-diol hydrochloride (200 mg, 0.4 mmol) in dry THF (2.5 ml) is treated with diisopropylethylamine (0.35 ml, 2 mmol) and cyclopropanecarboxylic acid chloride (0.036 ml, 0.4 mmol) and the mixture is stirred at room temperature for 48 hours. The solvent is removed under reduced pressure and the residue is purified by reverse-phase chromatography eluting with a gradient system of acetonitrile (0.1% TFA):water (0.1% TFA) (0:100 by volume) gradually changing to acetonitrile (0.1% TFA):water (0.1% TFA) (100:0 by volume) to afford the title compound. LCMS (electrospray): m/z [MH+] 533.25 1H nmr (MeOD, 400 MHz); 8.00(s, 1H), 7.40-7.25(m, 8H), 7.25-7.20(m, 2H), 4.75(m, 1H), 4.60(m, 1H), 4.50(m, 1H), 4.20(m, 2H), 4.00(m, 1H), 2.85(m, 1H), 2.10(m, 1H), 1.85(m, 1H), 0.95-0.80(m, 4H)

Provenance & Evidence