Reaktion #2446078

ord-2890cd91adef413792f014068d61a11e

Reaktionsgleichung

CC[C@H](C)[C@@H]([C@@H](CC(=O)N1CCC[C@H]1[C@H](OC)[C@@H](C)C(=O)N[C@@H](Cc1ccccc1)C(=O)O)OC)N(C)C(=O)[C@@H](NC(=O)[C@H](C(C)C)N(C)C)C(C)C.C[C@H](NC(=O)OC(C)(C)C)C(=O)O.[NH-]CCCO
Auristatin F hydroxypropylamide Boc-L-Alanine
O=C(O)C(F)(F)F
trifluoroacetic acid
→
CC[C@H](C)[C@@H]([C@@H](CC(=O)N1CCC[C@H]1[C@H](OC)[C@@H](C)C(=O)N[C@@H](Cc1ccccc1)C(=O)O)OC)N(C)C(=O)[C@@H](NC(=O)[C@H](C(C)C)N(C)C)C(C)C.C[C@H](N)C(=O)O.[NH-]CCCO
title compound
Ausbeute 92.0%
CC[C@H](C)[C@@H]([C@@H](CC(=O)N1CCC[C@H]1[C@H](OC)[C@@H](C)C(=O)N[C@@H](Cc1ccccc1)C(=O)O)OC)N(C)C(=O)[C@@H](NC(=O)[C@H](C(C)C)N(C)C)C(C)C.C[C@H](N)C(=O)O.[NH-]CCCO
Auristatin F hydroxypropylamide L-Alanine
Ausbeute 92.0%

Edukte

CC[C@H](C)[C@@H]([C@@H](CC(=O)N1CCC[C@H]1[C@H](OC)[C@@H](C)C(=O)N[C@@H](Cc1ccccc1)C(=O)O)OC)N(C)C(=O)[C@@H](NC(=O)[C@H](C(C)C)N(C)C)C(C)C.C[C@H](NC(=O)OC(C)(C)C)C(=O)O.[NH-]CCCO
Auristatin F hydroxypropylamide Boc-L-Alanine
O=C(O)C(F)(F)F
trifluoroacetic acid

Reagenzien

Keine

Lösungsmittel

ClCCl
dichloromethane

Reaktionsbedingungen

Temperatur
23°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigethe solvent removed under high vacuum
  2. 2
    Sonstigeprecipitation from diethyl ether (30 mL

Vorschrift

Auristatin F-hydroxypropylamide Boc-L-Alanine (112 mg, 0.115 mmol, prepared as described in Example 49) was taken up in dichloromethane (3 mL) and excess trifluoroacetic acid was added. The mixture was stirred at 23° C. for 1 hour and the solvent removed under high vacuum. The resulting oil was taken up in dichloromethane (1.5 mL) and precipitation from diethyl ether (30 mL to give the title compound as white solid (96.2 mg, 85%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08685383B2uspto-grants-2014_04