Sodium Hydroxide → HCID 117901319, compound

Participants

Reaction Steps

A solution of methyl ester 45 (2.00 g, 2.18 mmol) in MeOH/THF/H2O (60 mL/60 mL/20 mL) was charged with NaOH (436 mg, 10.9 mmol) and the reaction mixture was stirred at room temperature for 1 h. After completion of the reaction, the mixture was concentrated under reduced pressure and the pH of the solution was adjusted to 5 with 1 N HCl. The suspension was partitioned between CH2Cl2 (50 mL) and water (10 mL). The organic layer was separated and the aqueous layer was extracted with CH2Cl2 (2×50 mL). The combined organic extracts were dried over Na2SO4 and concentrated to afford compound 46 (1.90 g, 97%) as a white solid, which was used directly in the next step: 1H NMR (400 MHz, CD3OD) δ 4.08-4.00 (m, 1H), 3.98-3.89 (m, 2H), 3.27-3.10 (m, 4H), 3.02 (t, J=6.6 Hz, 2H), 1.86-1.65 (m, 4H), 1.64-1.24 (m, 14H), 1.43 (s, 18H), 1.42 (s, 18H).

Provenance & Evidence