Ammonium Chloride → HCID 178443787, compound

Participants

Reaction Steps

A mixture of diisopropyl (2RS,3SR)-2,3-epoxy-3(1-trityl-1,2,4-triazol-3-yl)propane phosphonate (6.83 g prepared as described in Example 51), sodium azide (4.18 g), ammonium chloride (1.51 g) and methanol-water (8:1, 125 ml) was heated under reflux for six hours, then concentrated under reduced pressure. The residue was filtered through silica in chloroform, then chromatographed on silica, using ethyl acetate-ethanol (20:1) as eluant, to give diisopropyl (2RS,3RS)-3-azido-2-hydroxy-3(1-trityl-1,2,4-triazol-3-yl)propane phosphonate (5.22 g, m.p. 137-139° C., after trituration with ether). IR (nujol): 3304, 2104 cm-1. NMR (CDCl3 : δ 1.3(12H,m), 1.9-2.25(2H,m), 4.17(1H,d), 4.45(1H,m), 4.68(2H,m), 4.78(1H,d), 7.1-7.4(15H,m), 7.98(1H,s). 13C NMR confirmed the regiochemistry.

Provenance & Evidence