Triethylamine → HCID 22877227, compound

Participants

Reaction Steps

(R)-2-Amino-1-propanol (0.23 g, 3.0 mmol), 9-(2,3,5-tri- O-benzoyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (1.7 g, 2.7 mmol) and triethylamine (0.30 g, 3.0 mmol) were dissolved in dioxan (20 ml) and stirred for 200 h at room temperature. Following purification by column chromatography, the resultant 2',3',5'-tri- O-benzoyl-2-chloro- N-[(R)-1-hydroxy-2-propyl]adenosine was deprotected using methanolic ammonia to provide the title 2-chloro- N-[(R)-1-hydroxy-2-propyl]adenosine as an amorphous foam (0.5 g, 54%), 1H NMR (DMSO-d6)δ 1.17 (3H, d, --CH3), 3.35-3.72 (4H, m, H-5'a, H-5'b and --CH2 --), 3.96 (1H, q, H-4'), 4.14 (1H, m, H-3'), 4.52 (1H, dd, H-2'), 5.08 (1H, t, 5'-OH), 5.22, 5.49 (2H, 2d, 2' and 3'-OH), 5.83 (1H, d, H-1'), 8.0 (1H, d, N--H) 8.40 (1H, s, H-8).

Provenance & Evidence