Hydrochloric Acid → HCID 57431262, compound

To a 50 mL flask containing (S)-methyl2-(bis(benzyloxy)phosphoryloxy)-3-methylbutanoate (699 mg, 1.78 mmol, 1.0 eq.) (prepared as in Example 18 or 19) was added methanol (9.2 mL). All starting material dissolved. Then a solution of potassium hydroxide in water (1 N, 3.56 mL, 3.56 mmol, 2.0 eq.) was added at ice-bath temperature. The resulting mixture was stirred at room temperature for 40 hrs. The reaction was monitored by LC-MS, and almost no starting remained. The reaction mixture was diluted with water (15 mL) and neutralized by hydrochloric acid (1 N, 3.6 mL, 3.6 mmol, 2.02 eq.) to reach pH 3 at 0° C. which was extracted by ethyl acetate (3×30 mL). The combined organic phase was washed with water (30 mL), brine (30 mL), and dried over Na2SO4 and concentrated under reduced pressure to afford crude compound 20, (S)-2-(bis(benzyloxy)phosphoryloxy)-3-methylbutanoic acid (650 mg) which was used directly in the next step without further purification. MS: m/z=379.0 (M+1).

1. dissolutionAll starting material dissolved
2. customat 0° C.
3. extractionwas extracted by ethyl acetate (3×30 mL)
4. washThe combined organic phase was washed with water (30 mL), brine (30 mL)
5. dry with materialdried over Na2SO4
6. concentrationconcentrated under reduced pressure

ORD record

ord-e8fa25e6858e41b79acaa815d6eb1470

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07960420B2