反応 #2446078

ord-2890cd91adef413792f014068d61a11e

反応方程式

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
収率 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
収率 92.0%

反応物

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

試薬

なし

溶媒

ClCCl
dichloromethane

反応条件

温度
23°CELSIUS
詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    その他the solvent removed under high vacuum
  2. 2
    その他precipitation from diethyl ether (30 mL

実験手順

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%).

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US08685383B2uspto-grants-2014_04