Octylamine → HCID 86689975, compound

To a solution of 2-acetoxy-4-(methylthio)butanoic acid (6.10 g, 31.7 mmol) in dichloromethane (100 mL) at 0° C. was added thionyl chloride (11.53 mL, 158.5 mmol) slowly over 30 min. The reaction was allowed to warm to room temperature with stirring overnight. The solvent was evaporated and the resulting oil was dried on the high vacuum for 3 hrs. To a solution of the resulting oil in dichloromethane (100 mL) at 0° C. was added triethylamine (8.84 mL, 63.4 mmol) and then octylamine (5.24 mL, 31.7 mmol) and the reaction was allowed to warm to room temperature with stirring overnight. The reaction was evaporated, redissolved in EtOAc (150 mL) and washed with 1N HCl (3×100 mL), saturated sodium bicarbonate (3×100 mL), and brine (1×100 mL). The organic layer was dried over magnesium sulfate, filtered and evaporated to give an oil. The oil was purified by silica gel chromatography with 0-30% EtOAc/heptane to give a yellow oil. (6.61 g, 69%). m/z 304 (MH+).

1. customThe solvent was evaporated
2. customthe resulting oil was dried on the high vacuum for 3 hrs
3. temperatureto warm to room temperature
4. stirringwith stirring overnight
5. customThe reaction was evaporated
6. dissolutionredissolved in EtOAc (150 mL)
7. washwashed with 1N HCl (3×100 mL), saturated sodium bicarbonate (3×100 mL), and brine (1×100 mL)
8. dry with materialThe organic layer was dried over magnesium sulfate
9. filtrationfiltered
10. customevaporated
11. customto give an oil
12. customThe oil was purified by silica gel chromatography with 0-30% EtOAc/heptane
13. customto give a yellow oil

ORD record

ord-0b4263263f834735a70b2acb8fca92db

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09169203B2