HCID 66778977, compound → HCID 66779277, compound

Participants

Reaction Steps

Using the general procedure (Method B) for the synthesis of nucleoside 5′-phosphoramidates to a solution of 250 mg of (3R,4R,5R)-2-(2-amino-6-methoxy-9H-purin-9-yl)-5-(hydroxymethyl)-3-methyltetrahydrofuran-3,4-diol in 5 mL of THF was added tert-BuMgCl (1.61 mL) followed by (2S)-cyclohexyl 2-(chloro(naphthalen-1-yloxy)phosphorylamino)-2-phenylacetate (1.10 g) in THF (5 mL). After workup and silica gel column chromatography, 310 mg of (2S)-cyclohexyl 2-((((2R,3R,4R)-5-(2-amino-6-methoxy-9H-purin-9-yl)-3,4-dihydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(naphthalen-1-yloxy)phosphorylamino)-2-phenylacetate was obtained (53% yield). HPLC tR=21.47, 21.65 min (column: Varian Pursuit XRs 5, C18, 150×4.6 mm; method: linear gradient of ACN (10% to 100%) in H2O in 30 min).

Provenance & Evidence