Hydrazine hydrate (1:1) → HCID 21478218, compound

Participants

Reaction Steps

2-(2-Benzothiazolylthio)ethylamine dihydrochloride was prepared by standard synthetic steps with a by Mitsunobu reaction between N-(2-hydroxyethyl)phthalimide and 2-mercaptobenzothiazole, followed by reaction with hydrazine hydrate. This amine dihydrochloride (0.52 g, 2.11 mmol) was reacted with 9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (0.79 g, 1.7 mmol), followed by deacylation of the purified 2',3',5'-tri-O-acetyl-N-[(R)-2(2-benzothiazolylthio)-1-ethyl]-2-chloroadenosine using sodium methoxide in methanol to provide the title N-[(R)-2-(2-benzothiazolylthio)-1-ethyl]-2-chloroadenosine as a foam after column chromatography, 1H NMR (DMSO-d6) δ 3.54-3.60 and 3.64-3.71 (4H, m, H-5'a and H-5'b and --CH2 --), 3.42, (2H, q, --CH2 --), 3.96 (1H, d, H-4'), 4.15 (1H, q, H-3'), 4.52 (1H, q, H-2'), 5.08 (1H, t, 5'-OH), 5.22, 5.51 (2H, 2d, 2'- and 3'-OH), 5.85 (1H, d, H-1'), 7.38, 7.48 (2H, 2t, Ar-H), 7.85, 8.02 (2H, 2d, Ar-H), 8.43 (1H, s, H-8), 8.68 (1H, t, N--H). HPLC retention time 18.5 min [gradient elution, 20-80% acetonitrile/water (containing 0.1% TFA)].

Provenance & Evidence