Hydrochloric Acid → HCID 10110107, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of Example 3E in THF (2.1 L) was treated with DPPA (90.5 g) and diisopropylethyl amine (56 mL), heated to reflux, stirred for 3 hours, cooled to 30° C., poured into ice cold 10% HCl, and stirred vigorously. The organic phase was treated with 10% HCl (500 mL) and NaCl (75 g). The aqueous phase was separated and washed with ethyl acetate. The extract was washed sequentially with water, saturated NaHCO3, and brine and concentrated. The concentrate was treated with toluene (550 mL), warmed to reflux, cooled to 35° C., treated with heptane (800 mL) over 2 hours, and filtered. The solid was dissolved in 1:1 THF/toluene (700 mL), and the resulting solution was washed with saturated NaHCO3 and brine, and concentrated. The solid was dried under vacuum (100 mm Hg) at 50° C. with a nitrogen bleed to provide 54.6 g of the desired product. 1H NMR (300 MHz, CDCl3) δ7.45 (m, 2H) 7.35 (m, 5H), 6.58 (m, 2H), 5.35 (br s, 1H), 5.05 (d, 1H, J=11 Hz), 4.94 (d, 1H, J=11 Hz), 3.85 (m, 1H), 3.73 (dd, 1H, J=7, 9 Hz), 3.55 (dd, 1H, J=7, 9 Hz), 3.51 (t, 1H, J=8 Hz), 3.25 (t, 1H, J=9 Hz).

Provenance & Evidence