Triethylamine → HCID 178520549, Verbindung

Temperatur

0 °C

To a dry flask under N2 atmosphere at 0° C. is added 1.31 g (11.3 mmol) of thiotetronic acid in 40 mL of dry dichloromethane followed by 1.42 mL (10.2 mmol) of triethylamine and 0.38 g (3.1 mmol) of 4-dimethylaminopyridine. After stirring at 0° C. for 5 minutes, 2.6 g (10.2 mmol) of cyclododecylbutanoic acid is added, followed by 4.8 g (11.3 mmol) of 1-cyclohexyl-3-(2-morpholinoethyl) carbodiimide metho p-toluenesulfonate. After stirring for 10 minutes, the reaction mixture is allowed to warm to room temperature and is stirred overnight. The reaction mixture is quenched with 1N HCl. The layers are separated and the aqueous phase is washed once with dichloromethane. The combined organic layers are washed twice with aqueous sodium bicarbonate and twice with aqueous 2N HCl. The organic phase is then dried over MgSO4 and the dichloromethane evaporated. The residue is flash chromatographed on acidic silica gel using 8% ether/hexanes, dissolved in ether, washed with 1N HCl, dried and evaporated to give 1.2 g of a white solid: m.p. 62°-69° C.; IR; NMR (CDCl3) δ 1.2-1.4 (m, 10H), 1.5 (s, 4H), 1.65 (m, 2H), 2.9 (t, 2H, J=7 Hz), 3.96 (s, 2H); MS.

1. stirringAfter stirring for 10 minutes
2. temperatureto warm to room temperature
3. stirringis stirred overnight
4. customThe reaction mixture is quenched with 1N HCl
5. customThe layers are separated
6. washthe aqueous phase is washed once with dichloromethane
7. washThe combined organic layers are washed twice with aqueous sodium bicarbonate and twice with aqueous 2N HCl
8. dry with materialThe organic phase is then dried over MgSO4
9. customthe dichloromethane evaporated
10. customchromatographed on acidic silica gel using 8% ether/hexanes
11. dissolutiondissolved in ether
12. washwashed with 1N HCl
13. customdried
14. customevaporated

ORD-Eintrag

ord-c9697368bb1d44f0b218071009af0f88

Quelldatensatz

uspto-grants-1995_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05468774