Reaktion #467419

ord-2c639d3b989d4981847829e087d2bb1f

Reaktionsgleichung

CC[C@H](C)[C@H](NC(=O)OC)C(=O)N[C@@H](Cc1ccccc1)[C@@H](O)CN(N)Cc1ccc(-c2ccccn2)cc1.Cl.Cl.Cl
1-[4-(pyridin-2-yl)-phenyl]-4(S)-hydroxy-2-amino-5(S)-N-(N-methoxycarbonyl-(L)-iso-leucyl)amino-6-phenyl-2-azahexane 3HCl
COC(=O)N[C@H](C(=O)O)C(C)C
N-methoxycarbonyl-(L)-valine
CN(C)C(On1ccccc1=O)=[N+](C)C.F[B-](F)(F)F
TPTU
C1CCC2=NCCCN2CC1
DBU
CN(C)C=O
DMF
CN(C)C=O
DMF
→
CC[C@H](C)[C@H](NC(=O)OC)C(=O)N[C@@H](Cc1ccccc1)[C@@H](O)CN(Cc1ccc(-c2ccccn2)cc1)NC(=O)[C@@H](NOC)C(C)C=C=O
title compound
CC[C@H](C)[C@H](NC(=O)OC)C(=O)N[C@@H](Cc1ccccc1)[C@@H](O)CN(Cc1ccc(-c2ccccn2)cc1)NC(=O)[C@@H](NOC)C(C)C=C=O
1-[4-(Pyridin-2-yl)-phenyl]-4(S)-hydroxy-2-N-(N-methoxy-carbonyl-(L)-valyl)amino-5(S)-N-(N-methoxycarbonyl-(L)-iso-leucyl)amino-6-phenyl-2-azahexane

Edukte

CC[C@H](C)[C@H](NC(=O)OC)C(=O)N[C@@H](Cc1ccccc1)[C@@H](O)CN(N)Cc1ccc(-c2ccccn2)cc1.Cl.Cl.Cl
1-[4-(pyridin-2-yl)-phenyl]-4(S)-hydroxy-2-amino-5(S)-N-(N-methoxycarbonyl-(L)-iso-leucyl)amino-6-phenyl-2-azahexane 3HCl
COC(=O)N[C@H](C(=O)O)C(C)C
N-methoxycarbonyl-(L)-valine
CN(C)C(On1ccccc1=O)=[N+](C)C.F[B-](F)(F)F
TPTU
C1CCC2=NCCCN2CC1
DBU
CN(C)C=O
DMF
CN(C)C=O
DMF

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

Analogously to Example 46, 0.96 g (1.5 mmol) of 1-[4-(pyridin-2-yl)-phenyl]-4(S)-hydroxy-2-amino-5(S)-N-(N-methoxycarbonyl-(L)-iso-leucyl)amino-6-phenyl-2-azahexane 3HCl (Example 47d) in 10 ml of DMF are reacted with 0.263 g (1.5 mmol) of N-methoxycarbonyl-(L)-valine, 0.446 g (1.5 mmol) of TPTU and 0.78 ml (4.5 mmol) of DBU in 7 ml of DMF. After working up, the title compound is obtained: TLC: Rf=0.4 (ethyl acetate); HPLC20-100: tRet=11.23. FAB MS (M+H)+=691.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06300519B1uspto-grants-2001_10