Hydrochloric Acid → HCID 13289108, compound

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.

1. dissolutionAll starting material dissolved
2. customwas removed under reduced pressure
3. extractionThe aqueous layer was extracted by ether (2×10 mL)
4. customat 0° C
5. extractionThe cloudy aqueous layer was extracted by ether (5×20 mL)
6. washThe combined organic phase was washed with brine (30 mL)
7. dry with materialdried over Na2SO4
8. concentrationconcentrated under reduced pressure

ORD record

ord-84907a4d00ec4077b8996624571cc7f5

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07960420B2