Water → HCID 86703815, compound

A reaction flask was cooled in an ice bath and charged with 6-mercaptohexanoic acid (500 mg, 3.37 mmol) and water (2 mL). The solution was stirred as methyl methanethiolsulfonate (468 mg, 3.71 mmol) dissolved in ethanol (1 mL) was added. The reaction was stirred overnight at room under an argon atmosphere. The reaction mixture was then diluted with saturated sodium chloride (400 mL) and extracted into ether (3×150 mL). The combined extracts were washed with the sodium chloride solution, dried over anhydrous sodium sulfate and concentrated in vacuo. The product was isolated via silica flash chromatography eluting with a 1:0.9:0.1 mixture of hexanes:ethyl acetate:acetic acid to give 482 mg (73.5% yield) of compound 53. 1H NMR (CDCl3, ref. 7.26 ppm) δ 1.473 (2H, m), 1.702 (4H, m), 2.359 (2H, t), 2.405 (3H, s), 2.708 (2H, t).

1. temperatureA reaction flask was cooled in an ice bath
2. additionwas added
3. extractionextracted into ether (3×150 mL)
4. washThe combined extracts were washed with the sodium chloride solution
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationconcentrated in vacuo
7. customThe product was isolated via silica flash chromatography
8. washeluting with a 1:0.9:0.1 mixture of hexanes

ORD record

ord-15db26cc69c8485583ea983385d370df

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09090629B2