Hydrochloric Acid → 4-[(1S)-1-[[(2R)-3-methyl-2-(2-phenoxyethoxy)butanoyl]amino]ethyl]benzoic acid

To a solution of methyl 4-[(1S)-1-[[(2R)-3-methyl-2-(2-phenoxyethoxy)butanoyl]amino]ethyl]benzoate (2.0 g, 5.01 mmol) in MeOH (25 mL) and THF (25 mL) is added 5N NaOH (10 mL, 50 mmol). The mixture is stirred at room temperature for 1.5 h, treated with 5N HCl (10 mL), and concentrated to remove organic solvents. The aqueous residue is extracted with ethyl acetate (3×30 mL). The combined ethyl acetate layers are dried with MgSO4, filtered, and concentrated. The crude material (1.36 g) is dissolved in ethyl acetate and washed with 1N NaOH (25 mL). The aqueous layer is extracted with ethyl acetate (25 mL), acidified with 1N HCl (25 mL), and extracted with ethyl acetate (3×25 mL). The combined ethyl acetate layers are dried with MgSO4, filtered, and concentrated to a waxy solid. This material is co-evaporated with MeOH (3×) to provide the title compound as a white solid (925 mg, 48%). MS (m/z): 386.2 (M+1).

1. concentrationconcentrated
2. customto remove organic solvents
3. extractionThe aqueous residue is extracted with ethyl acetate (3×30 mL)
4. dry with materialThe combined ethyl acetate layers are dried with MgSO4
5. filtrationfiltered
6. concentrationconcentrated
7. dissolutionThe crude material (1.36 g) is dissolved in ethyl acetate
8. washwashed with 1N NaOH (25 mL)
9. extractionThe aqueous layer is extracted with ethyl acetate (25 mL)
10. extractionextracted with ethyl acetate (3×25 mL)
11. dry with materialThe combined ethyl acetate layers are dried with MgSO4
12. filtrationfiltered
13. concentrationconcentrated to a waxy solid

ORD record

ord-3315b2f8cf344bd68d5b33544caa2dc8

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09000043B2