HCID 11234748, compound → HCID 11394346, compound

Participants

Reaction Conditions

Reaction Steps

The product from Example 145 (20 mg, 0.05 mmol) was dissolved into tetrahydrofuran (900 μL), cooled to 0° C., and treated with 1.0 M ethylmagnesium bromide in tetrahydrofuran (150 μL, 150 μmol). The reaction mixture was then stirred at room temperature overnight, quenched by the addition of saturated aqueous NH4Cl, and diluted with EtOAc. The aqueous phase was separated and extracted with EtOAc, and the combined organic phases were washed consecutively with 0.5 M aqueous dipotassium hydrogen phosphate and brine, concentrated, and purified by HPLC [Waters Nova-Pak HR C18 column (25 mm×100 mm, 6 μm particle size) using a gradient of 10% to 100% MeCN/0.1% aqueous TFA over 8 min (10 min run time) at a flow rate of 40 mL/min.] to provide the title compound (44% yield). MS (ESI APCI) m/z 362 (M+H)+; 1HNMR (300 MHz, CD3OD) δ 1.18 (d, 3H), 1.21 (t, 3H), 1.39-1.53 (m, 1H), 1.74-1.87 (m, 2H), 1.95-2.09 (m, 1H), 2.24-2.37 (m, 1H), 2.42-2.61 (m, 2H), 2.94-3.18 (m, 4H), 3.20-3.35 (m, 2H), 6.63 (s, 1H), 7.50-7.52 (m, 2H), 7.58 (dd, 1H), 7.77-7.79 (m, 1H), 7.87 (ddd, 1H), 7.96 (ddd, 1H), 8.22 (dd, 1H).

Provenance & Evidence