7,12-Dimethylbenz(a)anthracene → 1-[2-(3,5-Dichloro-4-hydroxy-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid (2-ethoxy-5-oxo-tetrahydro-furan-3-yl)-amide

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Reaction Steps

To a solution of 110 (1.94 mg, 0.36 mmol) in CH2Cl2 (5 ml) was added DMBA (70.7 mg, 0.45 mmol) and Pd(PPh3)4 (50.3 mg, 0.044 mmol) at 0° C. The solution was warmed to room temperature after 15 mins, stirred for 2 hours, diluted with CH2Cl2 then washed with water (2×) and brine. The organic layer was dried over anhydrous Na2SO4 and evaporated to give the crude product. Flash chromatography using CH2Cl2/MeOH (99/1 to 95/5%) afforded the title compound (138.6 mg, 77% yield). 1H-NMR (500 MHz, CD3OD) δ 1.13-1.31 (m, 3H), 1.35-1.49 (m, 3H), 1.84-2.35 (m, 4H), 2.43-3.0.5 (m, 2H) 3.48-3.93 (m, 4H), 4.22-4.80 (m, 3H), 5.38 (d, 0.4H), 5.46 (s, 0.1H), 5.55-5.61 (m, 0.5H), 7.76-7.94 (m, 2H). Analytical HPLC 8.70 min. LC-MS (ES+) m/e=502.2 (MH+).

Provenance & Evidence