Triethylamine → HCID 86689981, compound

Temperature

0 °C

To a solution of 2-acetoxy-4-(methylthio)butanoic acid (17.1 g, 89 mmol) in dichloromethane (350 mL) at 0° C. was added thionyl chloride (32.4 mL, 445 mmol) dropwise over 1 hr. The reaction was stirred at 0° C. for 1.5 hrs then the cooling bath was removed and the reaction was warmed to room temperature with stirring for 3 hrs. The solvent was evaporated and the resulting oil was dried under high vacuum for 1 hr to give an orange oil. A solution of the resulting oil in dichloromethane (˜30 mL) was added to a solution of triethylamine (24.8 mL, 178 mmol) and dodecylamine (20.5 mL, 89 mmol) in dichloromethane (150 mL) at 0° C. and the reaction was allowed to warm to room temperature with stirring overnight. The reaction was evaporated, re-dissolved in EtOAc (300 mL) and washed with 1N HCl (3×150 mL), saturated sodium bicarbonate (3×150 mL), and brine (1×150 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 0-40% EtOAc/heptane to give a yellow oil. (22.5 g, 70%). m/z 360 (MH+).

1. customthe cooling bath was removed
2. temperaturethe reaction was warmed to room temperature
3. stirringwith stirring for 3 hrs
4. customThe solvent was evaporated
5. customthe resulting oil was dried under high vacuum for 1 hr
6. customto give an orange oil
7. temperatureto warm to room temperature
8. stirringwith stirring overnight
9. customThe reaction was evaporated
10. dissolutionre-dissolved in EtOAc (300 mL)
11. washwashed with 1N HCl (3×150 mL), saturated sodium bicarbonate (3×150 mL), and brine (1×150 mL)
12. dry with materialThe organic layer was dried over magnesium sulfate
13. filtrationfiltered
14. customevaporated
15. customto give an oil
16. customThe oil was purified by silica gel chromatography with 0-40% EtOAc/heptane
17. customto give a yellow oil

ORD record

ord-81ea5a7916a54b6aac580d0283df2f15

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09169203B2