Reaktion #2370054

Reaktionsgleichung

Hunig's base

#6

tert-butyl (3R,4S,5S)-3-methoxy-5-methyl-4-[methyl(L-valyl)amino]heptanoate

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-N,2-dimethylalanine

HATU

→

#127

Ausbeute 78.2%

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-N,2-dimethylalanyl-N-[(3R,4S,5S)-1-tert-butoxy-3-methoxy-5-methyl-1-oxoheptan-4-yl]-N-methyl-L-valinamide

Ausbeute 78.2%

Lösungsmittel

dichloromethane

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeReaction
2. 2
   Waschenbefore being washed with 1 N HCl, and brine
3. 3
   TrocknenOrganics where then dried over sodium sulfate
4. 4
   Filtrationfiltered
5. 5
   SonstigeResidue was purified by Silica Chromatography (Gradient: 0%-30% acetone in heptane)

Vorschrift

To a round bottom flask containing #6 (4.7 g, 7.9 mmol, 1.0 eq.) and N-[(9H-fluoren-9-ylmethoxy)carbonyl]-N,2-dimethylalanine (3.2 g, 9.4 mmol, 1.2 eq.) and a stir bar under nitrogen, 50 mL of dichloromethane was added followed by HATU (3.6 g, 9.4 mmol, 1.2 eq.) and Hunig's base (5.5 mL, 32 mmol, 4.0 eq.). The reaction was allowed to stir at room temperature for ˜12 hours. Reaction was reduced to a smaller volume, taken up in ethyl acetate, before being washed with 1 N HCl, and brine. Organics where then dried over sodium sulfate, filtered and then reduced down onto silica. Residue was purified by Silica Chromatography (Gradient: 0%-30% acetone in heptane) producing #127 (4.2 g, 78%) as a white solid. LC-MS (Protocol Q): m/z 680.2 [M+H+] retention time=2.52 minutes.

Quelle