Methanol → 2-methyl-2-({2-[(3R)-oxolan-3-yl]ethyl}sulfanyl)propanoic acid

To a solution of 0.43 g (1.75 mmol) of ethyl 2-methyl-2-({2-[(3R)-oxolan-3-yl]ethyl}sulfanyl)propanoate in THF/water (4/1, 6.5 mL) are added 84 mg (3.49 mmol) of lithium hydroxide monohydrate. The reaction is stirred at room temperature for 18 h. Then methanol (0.5 mL) is added and the reaction is heated to 45° C. for 16 h. Additional lithium hydroxide monohydrate (83 mg, 3.49 mmol) is added and the reaction is heated to 55° C. for 3 h. The reaction mixture is partitioned between DCM (8 mL) and water (10 mL). The aqueous layer is cooled in an ice bath, acidified with 6M aqueous HCl solution to pH 1 and extracted with DCM (3×15 mL). The combined organic extracts are dried (MgSO4), filtered and the filtrate is concentrated under reduced pressure to afford 351 mg of 2-methyl-2-({2-[(3R)-oxolan-3-yl]ethyl}sulfanyl)propanoic acid. Yield: 92%; ES-MS: m/z 219 [M+H]; 1H NMR (250 MHz, CHLOROFORM-d) δ ppm 1.43-1.76 (9H, m), 1.96-2.16 (1H, m), 2.31 (1H, quin, J=7.31 Hz), 2.56-2.77 (2H, m), 3.37 (1H, dd, J=8.22, 7.16 Hz), 3.68-4.05 (3H, m), 7.62 (1H, br. s.)

1. temperaturethe reaction is heated to 45° C. for 16 h
2. temperaturethe reaction is heated to 55° C. for 3 h
3. customThe reaction mixture is partitioned between DCM (8 mL) and water (10 mL)
4. temperatureThe aqueous layer is cooled in an ice bath
5. extractionextracted with DCM (3×15 mL)
6. dry with materialThe combined organic extracts are dried (MgSO4)
7. filtrationfiltered
8. concentrationthe filtrate is concentrated under reduced pressure

ORD record

ord-3d118df16b964a188b99916ea2239185

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08372874B2