Triphenylphosphine → (5R)-3-[4-(3,6-dihydro-2H-pyran-4-yl)-3-fluoro-phenyl]-5-(1,2,5-thiadiazol-3-yloxymethyl)oxazolidin-2-one

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Reaction Steps

Diisopropylazodicarboxylate (0.22 g, 1.1 mmol) was added dropwise at ambient temperature to a stirred solution of 5(R)-hydroxymethyl-3-(4-[3,6-dihydro-(2H)-pyran-4-yl]-3-fluorophenyl)oxazolidin-2-one (WO97/09328; 0.275 g, 0.93 mmol), 3-hydroxy1,2,5-thiadiazole (Weinstock et al. Journal of Organic Chemistry 32, 2823 [1967]; 0.1 12 g, 1.1 mmol) and triphenylphosphine (0.288 g, 1.1 mmol) in dry THF (7 ml). The solution was kept for 1.5 hours. Solvent was evaporated and the residue was purified by flash column chromatography, eluting with EtOAc/isohexane (1:1) to give the title product (0.256 g , 73%) as a solid (mp 146-148 ° C.). MS: 378 (MH+); NMR: 2.4 (1H, bs); 3.78 (3H, t); 3.96 (1H, m); 4.2 (3H, m); 4.66 (2H, m); 5.1 (1H, m); 6.05 (1H, s); 7.27-7.5 (3H, m); 8.41 (1H, s).

Provenance & Evidence