Sodium Hydroxide → HCID 11163902, compound

Participants

Reaction Conditions

Reaction Steps

The product from Example 143C (755 mg, 2 mmol) was dissolved into ethanol (20 mL) and treated with 2 M aqueous NaOH (2 mL). The mixture was heated at 55° C. for 40 minutes, cooled to room temperature, concentrated, and partitioned between isopropanol and a mixture of 1 M aqueous potassium dihydrogen phosphate and brine. The aqueous phase was separated and extracted with isopropanol, and the combined organic phases were washed with a mixture of pH 6 potassium phosphate buffer and brine. The aqueous phase was separated and extracted with isopropanol, and the combined organic phases were washed with brine. Again, the aqueous phase was separated and extracted with isopropanol, and the combined organic phases were diluted with EtOAc, and filtered. The filtrate was dried (Na2SO4) and concentrated. The residue was chromatographed on silica with 50% EtOAc/CH2Cl2, followed by 10% MeOH/45% EtOAc/CH2Cl2, followed by 30% MeOH/CH2Cl2. The appropriate fractions were concentrated and the residue dissolved into EtOAc/CH2Cl2, and the solids which precipitated were washed with additional EtOAc/CH2Cl2 to provide the title compound as a white powder. MS (ESI APCI) m/z 350 (M+H)+; 1HNMR (300 MHz, CD3OD) δ 1.39 (s, 3H), 1.58-1.76 (m, 1H), 1.91-2.10 (m, 2H), 2.16-2.31 (m, 1H), 2.89-3.04 (m, 1H), 3.08-3.3 (m, 4H), 3.50-3.71 (m, 2H), 6.70 (s, 1H), 7.39-7.59 (m, 3H), 7.69 (d, 1H), 7.79 (s, 1H), 7.92 (d, 1H), 8.23 (s, 1H).]

Provenance & Evidence