Sodium Hydroxide → HCID 178454261, compound

Participants

Reaction Steps

A solution of methyl ester 48 (1.40 g, 1.32 mmol) in MeOH/THF/H2O (45 mL/45 mL/15 mL) was charged with NaOH (265 mg, 6.61 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 aqueous 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 49 (1.20 g, 87%) as a white solid, which was used directly in the next step: 1H NMR (400 MHz, CD3OD) δ 4.06-3.89 (m, 3H), 3.35 (t, J=7.6 Hz, 2H), 3.25-3.11 (m, 4H), 1.86-1.66 (m, 3H), 1.64-1.55 (m, 5H), 1.54-1.30 (m, 10H), 1.52 (s, 9H), 1.46 (s, 9H), 1.43 (s, 27H).

Provenance & Evidence