Ammonium Chloride → HCID 131718903, compound

Participants

Reaction Steps

A stirred mixture of diisopropyl(2RS,3RS)-2,3-epimino-3(1-trityl-1,2,4-triazol-3-yl)propane phosphonate (2.6 g, prepared as described in Example 58), sodium azide (1.59 g), ammonium chloride (0.58 g) and methanol-water (8:1, 50 ml) was heated under reflux for six hours, then allowed to stand at room temperture for three days. Further quantities of sodium azide (0.80 g) and ammonium chloride (0.29 g) were added and the mixture heated for a further six hours. It was then filtered through silica, using chloroform as eluant, dried, evaporated and chromatographed on silica, using chloroform-hexane-methanol (15:3:1) as eluant, to give diisopropyl(2RS,3SR)-2-amino-3-azido-3(1-trityl-1,2,4-triazol-3-yl)propane phosphonate (2.27 g) as a yellow oil. NMR (CDCl3): δ1.3(12H,m), 1.65-1.85(1H,m), 2.12-2.28(1H,m), 3.65(1H,m), 4.58(1H,d), 4.68(2H,m), 7.05-7.38(15H,m), 8.00(1H,s). Regiochemistry was confirmed by extensive NMR studies on acetylated material.

Provenance & Evidence