Ammonia → HCID 54568194, compound

Participants

Reaction Steps

The title compound was prepared according to method B as described in examples 4 and 5 by reacting O-[1,2,3,4-tetrahydronaphth-1-yl)hydroxylamine (prepared by the procedure described in example 6) (0.35 g, 2.0 mmol) with 9-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (1.0 g, 1.58 mmol) and debenzoylating the purified product using methanolic ammonia to provide the title 2-chloro-N-(1,2,3,4-tetrahydronaphth-1-yloxy)adenosine (0.10 g, 15%) (after column chromatography) as a colourless foam (a mixture of diastereoisomers), 1H NMR (DMSO-d6)γ 1.65 - 2.85 (6H, m,--CH2CH2CH2 --), 3.53-3.61 (1H, m, H-5'a), 3.64-3.70 (1H, m, H-5'b), 3.94 (1H, br d, H-4'), 4.16 (1H, br d, H-3'), 4.53 (1H, q, H-2'), 5.07 (2H, m, 5'-OH and OCH--), 5.26, 5.53 (2H, 2d, 2'- and 3'-OH), 5.88 (1H, d, H-1'), 7.13-7.30 (3H, m, Ar-H), 7.88-7.96 (1H, m, Ar-H), 8.52 (1H, s, H-8), 11.60 (1H, br s, N-H). HPLC retention time 20.71 and 20.95 min (gradient elution over 25 min.; 25-45% acetonitrile/0.1M.

Provenance & Evidence