Hydrochloric Acid → HCID 13289108, compound

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Reaction Steps

To a 50 mL flask containing methyl(S)-2-benzyloxy-3-methylbutanoate (309 mg, 1.39 mmol, 1.0 eq.) (prepared as in Example 24) was added methanol (9 mL). All starting material dissolved. Then a solution of potassium hydroxide in water (1 N, 4.2 mL, 4.2 mmol, 3.0 eq.) was added at ice-water bath temperature. The resulting mixture was stirred at room temperature for 3 days. The reaction was monitored by LC-MS, and almost no SM remained. The reaction mixture was diluted with water (15 mL) and most of methanol was removed under reduced pressure. The aqueous layer was extracted by ether (2×10 mL), and neutralized by hydrochloric acid (1 N, 4.2 mL, 4.2 mmol, 3.0 eq.) to reach pH 3 at 0° C. The cloudy aqueous layer was extracted by ether (5×20 mL). The combined organic phase was washed with brine (30 mL), dried over Na2SO4 and concentrated under reduced pressure to afford crude product (S)-2-benzyloxy-3-methylbutanoic acid (260 mg, 1.25 mmol, 90%). 1H NMR (300 MHz, CDCl3): consistent with proposed structure.

Provenance & Evidence