Triphenylphosphine → HCID 44218291, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-ethyl-4-(5-{3-[(ethyl-methyl-amino)-methyl]-5-methyl-phenyl}-[1,2,4]oxadiazol-3-yl)-6-methyl-phenol (99 mg, 271 μmol) in THF (2 mL), PPh3 (107 mg, 406 μmol) and (R)-2,2-dimethyl-1,3-dioxolane-4-methanol (36 mg, 271 μmol) were added. The mixture was cooled to 0° C. and DEAD (177 mg, 406 μmol, 186 μL of a 40% solution in toluene) was added. Stirring was continued at 0° C. for 10 min, then at rt for 1 h before another portion of PPh3 (107 mg, 406 μmol) and (R)-2,2-dimethyl-1,3-dioxolane-4-methanol (36 mg, 271 μmol) was added. Stirring was continued for 1 h and the reaction mixture was separated by prep. HPLC. The product containing fraction were combined, evaporated and dissolved in MeCN (1.5 mL) and 1N aq. HCl (0.4 mL). The mixture was stirred at rt for 10 min before it was again separated by prep. HPLC to give the title compound as a colourless resin (27 mg). LC-MS**: tR=0.56 min; [M+1]+=440.21; 1H NMR (D6-DMSO): δ 1.06 (t, J=7.0 Hz, 3H), 1.23 (t, J=7.0 Hz, 3H), 2.15 (s, 3H), 2.36 (s, 3H), 2.42-2.47 (m, 5H), 2.75 (q, J=7.3 Hz, 2H), 3.50 (d, J=4.8 Hz, 2H), 3.56 (s, 2H), 3.72-3.78 (m, 1H), 3.83-3.89 (m, 2H), 7.47 (s, 1H), 7.79 (s, 2H), 7.91 (s, 1H), 8.18 (s, 1H).

Provenance & Evidence