Triethylamine → HCID 24995241, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl (2S)-2-{[(4aR,6R,7R,7aR)-6-(4-amino-2-oxopyrimidin-1(2H)-yl)-7-hydroxy-7-methyl-2-oxidotetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-2-yl]amino}butanoate, prepared according the procedure described for Example 6, was diluted with a solution THF:DMF (5:2, 0.03 M). Et3N (4.0 eq.) and DMAP (0.2 eq.) were added then the mixture was cooled to 0° C. and 2-propylpentanoyl chloride (2.5 eq.) was added drop-wise. The mixture was immediately warmed to room temperature and stirred for 2 hours. The reaction was quenched by the addition of 1N HCl (aq) to bring the pH to 6, and then the solvent was removed in vacuum. The crude was purified by RP-HPLC (stationary phase: column Symmetry C18, 7 μm, 19×300 mm. Mobile phase: acetonitrile/H2O buffered with 0.1% TFA) to afford the title compound as white powder (36%).

Provenance & Evidence