Trifluoroacetic acid → HCID 11465090, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 36 (0.40 g) in CH2Cl2 (5 mL) at 0° C. was added dropwise TFA (5 mL) and the mixture was stirred at 0° C. for 2 h. Solvent was evaporated and coevaporated with CH2Cl2 (2×5 mL). The residue was suspended in Et2O/EtOAc (1:4 v/v, 10 mL) and treated with 1 M aqueous NaOH (10 mL). The aqueous phase was separated and acidified (pH ˜2-3) with aqueous HCl. The mixture was extracted with EtOAc and the organic layer was dried (Na2SO4) and concentrated. The resulting solid foam was dissolved in a small amount EtOAc and then excess hexanes added. After stirring for 20 min, the precipitate was filtered and washed with hexanes to provide 35 (0.31 g, 86%) as a pale yellow solid, mp 181-183° C. 1HNMR (CD3OD): δ 0.92 (t, J=7.1 Hz, 3H), 2.47 (q, J=7.1 Hz, 2H), 6.49 (d, J=16 Hz, 1H), 6.82-6.87 (m, 4H), 7.03-7.21 (m, 5H), 7.27 (d, J=7.8 Hz, 2H), 7.6 (d, J=7.8 Hz, 2H), 7.69 (d, J=16 Hz, 1H); 31PNMR (CD3OD): δ−4.06 (s); MS, m/z 473 (M+Na)+; Anal. calculated for C25H23O6P.0.36H2O: C, 65.72; H, 5.23; Found: C, 65.71; H, 5.33.

Provenance & Evidence