Sodium Thiosulfate → HCID 86585878, compound

Participants

Reaction Steps

1,1,1-Triacetoxy-1,1-dihydro-1,2-benzodioxol-3(1H)-one (273 mg, 0.64 mmol) was added in one portion to a stirred solution of 3-benzoylamino-5-fluoro-4-hydroxy-pentanoic acid tert-butyl ester (100 mg, 0.32 mmol) (prepared from benzoic acid and 3-amino-5-fluoro-4-hydroxy-pentanoic acid tert-butyl ester using standard coupling procedures eg. HOBT, DMAP, and EDC) in dry dichloromethane (DCM) (2 ml) at 0° C. The mixture was brought to room temperature (r.t.) during 16 h, diluted with EtOAc, then poured into a 1:1 mixture of saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium thiosulphate. The organic layer was removed and the aqueous layer re-extracted with EtOAc. The combined organic organic extracts were dried (Na2SO4) and concentrated. The residue was purified by flash chromatography (30% EtOAc in hexane) to afford the title compound as a colourless gum (94 mg, 95%): 1H NMR (CDCl3) δ 7.80 (2H, m), 7.50 (4H, m), 5.2 (3H, m), 2.95 (2H, m), 1.45 (9H, s); 13C NMR (CDCl3) δ 203.19, 203.02, 171.02, 167.57, 133.54, 133.04, 132.60, 129.16, 127.97, 127.53, 85.52, 83.70, 82.80, 53.13, 53.03, 36.63, 36.61, 28.44, 28.37; 19F NMR (CDCl3) δ −232.09(t, J 49 Hz).

Provenance & Evidence