2-Thiophenethiol → HCID 22858277, compound

Participants

Reaction Steps

The title compound was prepared according to method A as described in Example 1 by reacting 2-[(R)-2-amino-1-propylthio]thiophene hydrochloride [prepared by a Mitsunobu reaction as described in Example 1 using 2-[(R)-N-tert-butyloxycarbonyl]amino-1-propanol (7.53 g, 43 mmol) and 2-mercaptothiophene (5.00 g, 43 mmol) followed by acidic hydrolysis] (0.63 g, 3.0 mmol) with 9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (1.12 g, 2.5 mmol), followed by deacylation of the purified 2',3',5'-tri-O-acetyl-2-chloro-N-[(R)-1-(2-thienyl)thio-2-propyl]adenosine using sodium methoxide in methanol to provide the title 2-chloro-N-[(R)-1-(2-thienyl)thio-2-propyl]adenosine (0.95 g, 82%) as a foam after column chromatography. 1H NMR (DMSO-d6) δ1.26 (3H, d, --CHCH3), 2.95-3.18 (2H, ABX, --CH2 --S--), 3.55 and 3.61 (2H, ABX, H-5'a and H-5'b ), 3.95 (1H, q, H-4), 4.14 (1H, t, H-3'), 4.44 (1H, m, --CH--CH3), 4.54 (1H, t, H-2'), 5.84 (1H, d, H-1'), 7.03 (1H, t, Ar--H), 7.23, 7.61 (2H, 2d, Ar--H), 8.38 (1H, d, --NH), 8.42 (1H, s, H-2). HPLC retention time 19.5 min [gradient elution, 20-80% acetonitrile/water (containing 0.1% TFA)].

Provenance & Evidence