Reaktion #59815

Reaktionsgleichung

amino acid

N,N′-Bis-(2-carbethoxyethyl)-N,N′-bis-(tert-butoxycarbonyl)-1,4-diaminobutane

dimethylaminopyridine

oleyl alcohol

EDCI

→

ester

Ausbeute 99.5%

3-(tert-Butoxycarbonyl-{4-[tert-butoxycarbonyl-(2-octadec-8-enyloxycarbonyl-ethyl)-amino]-butyl}-amino)-propionic acid octadec-8-enyl ester

Ausbeute 99.5%

Lösungsmittel

dichloromethane

dichloromethane

Dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeat 0° C
2. 2
   Waschenthe mixture was washed with brine (4×200 mL)
3. 3
   Trocknendried (Na2SO4)
4. 4
   Einengenconcentrated in vacuo
5. 5
   Sonstigeto leave an oil which
6. 6
   Sonstigewas purified by column chromatography
7. 7
   Wascheneluting with a solvent gradient of CH2Cl2 (50-90%) in hexane

Vorschrift

To a solution of the N-protected amino acid 4 (n=4; 15.2 g, 35.1 mmol), dimethylaminopyridine (1.70 g, 14.0 mmol) and oleyl alcohol (18.4 g, 68.4 mmol) in dichloromethane (200 mL) was added a solution of EDCI (13.1 g, 68.4 mmol), in dichloromethane (50 mL) at 0° C. The resulting mixture was allowed to warm to room temperature and then stirred under N2 for 18 h. Dichloromethane (250 mL) was added and the mixture was washed with brine (4×200 mL), dried (Na2SO4) and concentrated in vacuo to leave an oil which was purified by column chromatography eluting with a solvent gradient of CH2Cl2 (50-90%) in hexane to afford the ester 5 as a colourless oil (13.0 g, 40%).

Quelle