Triethylamine → HCID 178451424, compound

Participants

Reaction Steps

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile (BOC-ON, 2.82 g) was added portionwise to a stirred solution of diisopropyl (2RS,3RS)-2,3-epimino-3(1-trityl-1,2,4-triazol-3-yl)propane phosphonate (2.76 g, prepared as described in Example 58) and triethylamine (2.17 ml) in dioxan-water (2:1, 75 ml). The mixture was stirred at room temperature for seven hours, allowed to stand for a further three days, diluted with water (50 ml) and extracted with chloroform (3×50 ml). The organic layers were dried over magnesium sulphate and evaporated under reduced pressure. The residue was purified using HPLC on silica, with ethyl acetate as eluant, to give diisopropyl (2RS,3RS)-2,3(N-tert-butoxycarbonylepimino-3(1-trityl-1,2,4-triazol-3-yl)propane phosphonate (1.22 g, m.p. 30°-31° C.). NMR (CDCl3): δ 1.25(12H,m), 1.33(9H,s), 1.70(1H,m), 2.23(1H,m), 3.35(1H,m), 3.53(1H,d), 4.68(2H,m), 7.1-7.4(15H,m), 7.85(1H,s). IR: 1724 cm-1.

Provenance & Evidence