Triethylamine → HCID 22877228, compound

Participants

Reaction Steps

(R)-1-Phenylsulphonyl-2-propylamine (0.4 g, 1.7 mmol) was reacted with 9-(2,3,5-tri- O-benzoyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (1.7 g, 1.0 mmol) in dioxan (20 ml) in the presence of triethylamine (0.4 g, 4.3 mmol). The reaction mixture was stirred at room temperature for 48 h, heated at 60° C. for 4 h, cooled, filtered and evaporated. The product (after purification by flash chromatography) was debenzoylated with methanolic ammonia to provide the title 2-chloro- N-[(R)-1-phenylsulphonyl-2-propyl]adenosine (after column chromatography) as a foam (0.2 g, 24%), 1H NMR (DMSO-d6)δ 1.24 (3H, d, --CH3), 3.45 (1H, dd, --C--H), 3.53-3.61 (2H, m, H-5'a and --C--H), 3.64-3.71 (1H, m, H-5'b), 3.86 (1H, dd, --C--H), 3.97 (1H, q, H-4'), 4.14 (1H, m, H-3'), 4.53 (1H, m, H-2'), 5.09 (1H, t, 5'-OH), 5.23, 5.50 (2H, 2 d, 2' and 3'-OH), 5.83 (1H, d, H-1'), 7.45-7.82 (5H, m, Ar--H), 8.21 (1H, s, --N--H), 8.38 (1H, s, H-8).

Provenance & Evidence