Sodium Hydroxide → HCID 178454263, compound

Participants

Reaction Steps

A solution of methyl ester 20 (6.00 g, 8.21 mmol) in MeOH/THF/H2O (100 mL/100 mL/50 mL) was charged with NaOH (1.64 g, 41.1 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 (150 mL) and water (100 mL). The organic layer was separated and the aqueous layer was extracted with CH2Cl2 (2×150 mL). The combined organic extracts were dried over Na2SO4 and concentrated to afford compound 21 (5.50 g, 94%) as a white solid, which was used directly in the next step: 1H NMR (400 MHz, CD3OD) δ 4.06-4.00 (m, 1H), 4.00-3.93 (m, 1H), 3.35 (t, J=7.3 Hz, 2H), 3.26-3.07 (m, 2H), 1.85-1.56 (m, 6H), 1.53-1.32 (m, 6H), 1.52 (s, 9H), 1.46 (s, 9H), 1.438 (s, 9H), 1.435 (s, 9H).

Provenance & Evidence