Lithium hydroxide, monohydrate → HCID 59268002, compound

To a solution of 2.17 g (6.18 mmol) of ethyl 2-methyl-2-{[(2S)-oxan-2-ylmethyl]sulfanyl}propanoate (70%) in THF/water (1/1, 40 mL) are added 1.39 g (18.52 mmol) of lithium hydroxide monohydrate. The reaction is stirred at room temperature for 2 d, then concentrated under reduced pressure to remove the organic solvent. The aqueous residue is washed with diethyl ether (200 mL), then acidified with 6N aqueous HCl solution and extracted with ethyl acetate (3×20 mL). The combined organic extracts are dried (MgSO4), filtered and the filtrate is concentrated under reduced pressure to give 2.07 g of 2-methyl-2-{[(2S)-oxan-2-ylmethyl]sulfanyl}propanoic acid (58 wt % by NMR, residual solvent). Yield: 89%, ES-MS: m/z 219 [M+H]; 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 1.29-1.42 (1H, m), 1.45-1.61 (9H, m), 1.65-1.73 (1H, m), 1.80-1.90 (1H, m), 2.71-2.75 (1H, m), 2.78-2.84 (1H, m), 3.37-3.49 (2H, m), 4.00 (1H, dt, J=11.41, 2.16 Hz).

1. concentrationconcentrated under reduced pressure
2. customto remove the organic solvent
3. washThe aqueous residue is washed with diethyl ether (200 mL)
4. extractionextracted with ethyl acetate (3×20 mL)
5. dry with materialThe combined organic extracts are dried (MgSO4)
6. filtrationfiltered
7. concentrationthe filtrate is concentrated under reduced pressure

ORD record

ord-887e7689e00c4e01ba497e5ca88a9861

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08362039B2