Dicyclohexylcarbodiimide → HCID 71243538, Verbindung

To a solution of 4-{[(1′S,2′S)-1′-hydroxy-1′,3′-dihydro-1H,2′H-2,2′-biinden-2′-yl]methyl}-N-methylbenzamide (22, 150 mg, 0.38 mmol), DCC (94 mg, 0.45 mmol) and DMAP (5 mg, 0.038 mmol) in ethyl acetate (10 mL), was added Fmoc leucine (134 mg, 0.38 mmol) and then stirred at room temperature for 12 h. The solids were filtered, washed with ethyl acetate (25 ml) and the combined filtrate was washed with 1.5 N HCl (25 mL), water (25 mL), brine (10 mL), dried over anhydrous Na2SO4. The organic layer was evaporated under reduced pressure and the residue 1 (180 mg) was dissolved in dry THF (5 mL) and cooled to 0° C. Dimethylamine (5 mL, 20% in THF) was added drop wise and the reaction mixture was slowly allowed to stir at room temperature for 1 h. The reaction mixture was evaporated under reduced pressure and the residue was purified by CombiFlash using 10% methanol in chloroform as an eluent to yield 75 mg (39%) of the title compound as an off white solid.

1. filtrationThe solids were filtered
2. washwashed with ethyl acetate (25 ml)
3. washthe combined filtrate was washed with 1.5 N HCl (25 mL), water (25 mL), brine (10 mL)
4. dry with materialdried over anhydrous Na2SO4
5. customThe organic layer was evaporated under reduced pressure
6. dissolutionthe residue 1 (180 mg) was dissolved in dry THF (5 mL)
7. temperaturecooled to 0° C
8. additionDimethylamine (5 mL, 20% in THF) was added drop wise
9. stirringto stir at room temperature for 1 h
10. customThe reaction mixture was evaporated under reduced pressure
11. customthe residue was purified by CombiFlash

ORD-Eintrag

ord-60262c5367834c0fa1e2d9f7c0478220

Quelldatensatz

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09260376B2