Water → HCID 10839225, compound

Participants

Reaction Steps

The product of Example 304F (291 mg, 0.56 mmol) was dissolved in THF(4 mL) and saturated aqueous LiOH (1 mL). Water (1 mL) was added and the reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was thoroughly evaporated and formic acid was added to pH3 The reaction was evaporated to dryness and ethyl acetate (10 mL) was added followed by a minimum quantity of H2O (−1 mL) to completely solubilize the free acid and the water soluble salts, respectively. The layers were separated and the aqueous layer was extracted with ethyl acetate (3×). The ethyl acetate layers were combined and dried over Na2SO4, filtered, and evaporated and then lyophilized to give the title compound (242 mg, 86%) as an amorphous white solid. 1H NMR (300 MHz, CD3OD) δ 8.30 (bs, 1H), 8.14 (m, 1H), 7.76-7.33 (m, 9H), 5.28 (s, 2H), 4.87-4.40 (m, 1H), 2.40-2.06 (m, 2H), 2.04-1.94 (m, 4H contains methionine SMe), 1.92-1.80 (m, 1H). MS (CI) 505 (M+H)+ 505. Anal calcd for C25H23O4N2SF3: 0.65H2O solvate: C, 58.17; H, 4.74; N, 5.43. Found: C, 58.17; H, 4.80; N, 5.31. HRMS FAB Calcd m/z MH+ for C25H23O4N2SF3 505.1409, found 505.1408.

Provenance & Evidence