反応 #969876

ord-0b684c819b1449a88100176c90eb6a4f

反応方程式

C1CCNCC1
piperidine
CC(C)[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)N1CCC[C@H]1C(=O)O.COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1
Fmoc-Val-Pro doxorubicin
CC(C)[C@H](N)C(=O)N1CCC[C@H]1C(=O)O.COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1
compound G
収率 50.0%
CC(C)[C@H](N)C(=O)N1CCC[C@H]1C(=O)O.COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1
H-Val-Pro doxorubicin
収率 50.0%

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    その他form red to purple)
  2. 2
    その他Then, the reaction mixture was evaporated to dryness under reduced pressure
  3. 3
    その他the residue thus obtained
  4. 4
    その他was purified by reverse phase chromatography with water/acetonitrile (70:1)

実験手順

A solution of piperidine in dimethylformamide 50% (1.92 mL) was added to Fmoc-Val-Pro-doxorubicin (F) (29.7 mg, 0.03 mmol) and the reaction mixture was stirred at room temperature for 1 minute (the reaction colour changes form red to purple). Then, the reaction mixture was evaporated to dryness under reduced pressure and the residue thus obtained was purified by reverse phase chromatography with water/acetonitrile (70:1) to give the deprotected compound G (50% yield)

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US08236756B2uspto-grants-2012_08