Ammonia → HCID 54000395, compound

Participants

Reaction Steps

(R)- or (S)-9-[3-t-butyldiphenylsilyloxy-2-(diethoxyphosphorylmethylthio)propoxy]di-t-butoxycarbonylamino-6-methoxypurine (0.45%, 0.52 mmol) was added to a mixture of water (1.5 ml) and trifluoroacetic acid (4.5 ml), and the mixture was stirred at room temperature for 3 hr. The solution was then treated with saturated ethanolic ammonia solution to bring the pH to 11. The solution was extracted with chloroform (3×50 ml) and the organic layers were combined and dried (MgSO4). After filtration and evaporation in vacuo the residue was purified by column chromatography on silica, eluting with chloroform : methanol (95:5) to give (R) or (S)-2-Amino-9-[2-(diethoxyphosphorylmethylthio)-3-hydroxypropoxy]-6-methoxypurine as a colourless gum (0.16 g, 72%). υmax (film) 3340, 3220, 3120, 2980, 1620, 1585, 1500, 1480, 1450, 1390, 1330 and 1260 cm-1 ; 1H NMR δH [(CD)3SO] 1.22 (δH t, J 6Hz, CH3 × 2) 3.06 (2H,d, J=12.5Hz, PCH2S), 3.35 (1H, m, CH of CH2), 3.66 (1H, m, CH of CH2), 3.8 (1H, m, CH),3.96 (3H, s, OCH3), 4.02 (4H, m, CH2 ×2), 4.46 (2H, m, CH2), 5.06 (1H, t, J ™5.5Hz, D2O exchangeable OH), 6.6 (2H, brs, D2O exchangeable NH2), 8.1 (1H, s, 8-H): (Found: C, 39.03; H,5.70; N15.89 %. C14H24N5O6PS (0.5 H2O ) requires: C,39.06; H,5.80, N,16.24%; MS.(70eV): m/z=422 (MH+); [α] 25 CHCl3) (S)-enantiomer ™+1.8°; (R)-enantiomer=-1.3°.

Provenance & Evidence