Diisopropylethylamine → 2-Dimethylamino-4-methyl-pentanoic acid [2-(4-benzyloxy-phenyl)-1-morpholin-4-ylmethyl-ethyl]-amide

Temperatur

0 °C

(S)-2-Dimethylamino-4-methyl-pentanoic acid (55.3 mg, 0.347 mmol) was dissolved in dry DMF (3 mL) under nitrogen atmosphere and cooled to 0° C. in an ice-water bath. To this solution were added in succession N,N-diisopropylethylamine (0.180 mL, 1.04 mmol) and solid O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate (132 mg, 0.347 mmol, Novabiochem, La Jolla, Calif.). The resulting reaction mixture was stirred at that temperature for 30 minutes, (S)-2-(4-benzyloxy-phenyl)-1-morpholin-4-ylmethyl-ethylamine (153 g, 0.347 mmol, Example 3, Step D) was then added. After an additional 60 minutes stirring at 0° C., the reaction mixture was mixed with 60 mL of diethyl ether, and the resulting mixture was successively washed with saturated aqueous NaHCO3 solution and brine and then dried over Na2SO4. The solution was concentrated in vacuo, an oil was obtained. The crude product was purified by chromatography (silica gel, 10% methanol in chloroform) to give the title compound as a white solid (90 mg, 55%); mp 113-114° C.

1. customThe resulting reaction mixture
2. stirringAfter an additional 60 minutes stirring at 0° C.
3. washthe resulting mixture was successively washed with saturated aqueous NaHCO3 solution and brine
4. dry with materialdried over Na2SO4
5. concentrationThe solution was concentrated in vacuo
6. customan oil was obtained
7. customThe crude product was purified by chromatography (silica gel, 10% methanol in chloroform)

ORD-Eintrag

ord-4d0a204cee834681801341e99aaf1ba9

Quelldatensatz

uspto-grants-2002_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06362174B1