Triethylamine → (+/-)-N-[2,6-Bis(1-methylethyl)phenyl]-2-dodecyl-alpha-fluoro-alpha-phenyl-2H-tetrazole-5-acetamide

Temperatur

0 °C

Oxalyl chloride (0.08 mL, 0.92 mole) was added to a stirred solution of 2-dodecyl-α-fluoro-α-phenyl-2H-tetrazole-5-acetic acid (0.24 g, 0.61 mmole) in 5 mL of CH2Cl2 at room temperature. The mixture was stirred 60 minutes, the one drop of DMF was added (immediate gas evolution). The solution was stirred overnight, concentrated (rotovap), toluene was added, and the solution concentrated again. The residue was dissolved in CH2Cl2 (3 mL) and added to a stirred solution of 2,6-diisopropylaniline (0.12 mL, 0.61 mmole) and Et3N (0.14 mL, 1.0 mole) in CH2Cl2 (2 mL) cooled to 0° C. under dry nitrogen. After 20 minutes, the ice bath was removed and the solution allowed to warm to room temperature and stirred for 3 days. The mixture was then diluted with ethyl acetate (150 mL) and washed with dilute HCl (50 mL), bicarbonate (50 mL), brine (50 mL), and dried. Filtration and concentration afforded an oil which was flash chromatographed (silica gel, 10:1 hexanes-ethyl acetate) to produce 150 mg of the title compound as an oil which solidified on standing.

1. stirringThe solution was stirred overnight
2. concentrationconcentrated (rotovap), toluene
3. additionwas added
4. concentrationthe solution concentrated again
5. dissolutionThe residue was dissolved in CH2Cl2 (3 mL)
6. waitAfter 20 minutes
7. customthe ice bath was removed
8. temperatureto warm to room temperature
9. stirringstirred for 3 days
10. additionThe mixture was then diluted with ethyl acetate (150 mL)
11. washwashed with dilute HCl (50 mL), bicarbonate (50 mL), brine (50 mL)
12. customdried
13. filtrationFiltration and concentration
14. customafforded an oil which
15. customchromatographed (silica gel, 10:1 hexanes-ethyl acetate)

ORD-Eintrag

ord-5d0095a3b0aa48519a96fcc0c54b5e30

Quelldatensatz

uspto-grants-1997_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05646170