Reaktion #467381

Reaktionsgleichung

1-[4-(thiazol-5-yl)-phenyl]-4(S)-hydroxy-2-amino-5(S)-N-(N-methoxycarbonyl-(L)-iso-leucyl)amino-6-phenyl-2-azahexane

NMM

N-methoxycarbonyl-(L)-tert-leucine

TPTU

→

title compound

1-[4-(Thiazol-5-yl)-phenyl]4(S)-hydroxy-2-N-(N-methoxycarbonyl-(L)-tert-leucyl)amino-5(S)-N-(N-methoxycarbonyl-(L)-iso-leucyl)amino-6-phenyl-2-azahexane

Lösungsmittel

ethyl acetate

DMF

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe aqueous phase is separated off
2. 2
   Extraktionextracted with ethyl acetate
3. 3
   WaschenThe organic phases are washed 2× with water and brine
4. 4
   Trocknendried (Na2SO4)
5. 5
   Einengenconcentrated by evaporation
6. 6
   SonstigeColumn chromatography (SiO2; ethyl acetate) and crystallisation from ethyl acetate/ether/hexane

Vorschrift

Under argon, 0.5 mmol of 1-[4-(thiazol-5-yl)-phenyl]-4(S)-hydroxy-2-amino-5(S)-N-(N-methoxycarbonyl-(L)-iso-leucyl)amino-6-phenyl-2-azahexane and 165 μl (1.5 mmol) of NMM in 4.8 ml of DMF are added to 113.5 mg (0.60 mmol) of N-methoxycarbonyl-(L)-tert-leucine (Example 2e) and 149 mg (0.50 mmol) of TPTU in 2.5 ml of DMF and the mixture is stirred at room temperature for 14 hours. Ice-water and and ethyl acetate are added; the aqueous phase is separated off and extracted with ethyl acetate. The organic phases are washed 2× with water and brine, dried (Na2SO4) and concentrated by evaporation. Column chromatography (SiO2; ethyl acetate) and crystallisation from ethyl acetate/ether/hexane yield the title compound: TLC: Rf=0.42 (methylene chloride/ethanol 10:1); HPLC20-100: tRet=14.8; FAB MS (M+H)+=711.

Quelle