Reaktionsgleichung
[OH:1]N1C(=O)CCC1=O.[CH3:9][CH:10]([CH3:17])[N:11]=[C:12]=[N:13][CH:14]([CH3:16])[CH3:15].N(C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)CC(O)=O>ClCCl>[CH:10]([NH:11][C:12]([NH:13][CH:14]([CH3:16])[CH3:15])=[O:1])([CH3:17])[CH3:9]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
N-Hydroxysuccinimide (1.70 g, 14.77 mmol) and DIC (1.87 g, 14.77 mmol) were added sequentially to a stirred solution of Fmoc-Gly-OH (4.0 g, 13.45 mmol) in dichloromethane (15 mL); the resulting mixture was stirred at room temperature for 4 h. The N,N′-diisopropylurea formed was removed by filtration and the solid was washed with ether (20 mL). The volatiles were removed and the solid Fmoc-Gly-succinimidyl ester formed was washed with ether (3×20 mL). Fmoc-Gly-succinimidyl ester was then redissolved in dry DMF (15 mL) and 3-aminodeoxycholic acid (5.21 g, 12.78 mmol) was added to the clear solution. The reaction mixture was stirred at room temperature for 4 h, water (200 mL) was added and the precipitated solid was filtered, washed with water, dried and purified by silica gel chromatography (TLC (silica): (Rf: 0.50, silica gel, CH2Cl2/CH3OH, 9:1) (eluant: CH2Cl2/CH3OH (9:1)) to give (3β,5β,7α,12α)-3-[[(9H-Fluoren-9-ylmethoxy)amino]acetyl]amino-7,12-dihydroxycholan-24-oic acid as a colorless solid. Yield: 7.46 g (85%).
Quellen und Nachweise
- ORD-Eintrag
- ord-10908cd89ed44440b9df594647cb51e0
- Quelldatensatz
- uspto-grants-2013_05
- Patentnummer
- US08444954B2
Verknüpfte Notizen
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