Hydrochloric Acid → HCID 22858287, compound

Participants

Reaction Steps

2-[(R)-2-(N-tert-Butyloxycarbonylamino)-1-propylsulphonyl]benzothiazole was prepared by oxidation of 2-[(R)-2-(N-tert-butyloxycarbonylamino)-1-propylthio]benzothiazole (see Example 5) (0.55 g, 1.7 mmol) with "Oxone" on a Montmorillionite support. A mixture of the sulphonyl and sulphinyl derivatives was obtained, and the 2-[(R)-2-(N-tert-butyloxycarbonylamino)-1-propylsulphonyl]benzothiazole was isolated following column chromatography. Deprotection was performed under standard conditions with hydrogen chloride in ethyl acetate. The resultant 2-[(R)-2-aminopropyl-1-propylsulphonyl]benzothiazole hydrochloride (0.088 g, 0.4 mmol) was reacted with 9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (0.18 g, 0.4 mmol), followed by deacylation of the purified 2',3',5'-tri-O-acetyl-N-[(R)-1-(2-benzothiazolyl)sulphonyl-2-propyl]-2-chloroadenosine using sodium methoxide in methanol provided the title N-[(R)-1-(2-benzothiazolyl)sulphonyl-2-propyl]-2-chloroadenosine as a foam (following column chromatography); 1H NMR (DMSO-d6) δ 1.83 (3H, d, --CHCH3), 3,55, 3.66 (2H, ABX, H- 5'a and H-5'b), 3.96 (1H, q, H-4'), 4.17 (1H, q, H-3'), 4.59 (1H, q, H-2'), 5.08 (1H, t, 5'-OH), 5.24, 5.68 (2H, 2d, 2'- and 3'-OH), 5.95 (1H, d, H-1'), 7.34, 7.47 (2H, 2t, Ar-H), 7.84, 8.01 (2H, 2d, Ar-H), 8.14 (1H, t, N--H), 8.71 (1H, s, H-8). HPLC retention time 13.5 min [gradient elution, 20-80% acetonitrile/water (containing 0.1% TFA)].

Provenance & Evidence