反应 #2446078

ord-2890cd91adef413792f014068d61a11e

反应方程式

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
收率 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
收率 92.0%

反应物

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

试剂

无

溶剂

ClCCl
dichloromethane

反应条件

温度
23°CELSIUS
详细条件
See reaction.notes.procedure_details.

后处理

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

实验过程

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%).

来源

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