Réaction #969876

ord-0b684c819b1449a88100176c90eb6a4f

Équation de réaction

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
Rendement 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
Rendement 50.0%

Réactifs

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

Réactifs

Aucun

Solvants

CN(C)C=O
dimethylformamide

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

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

Mode opératoire

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)

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US08236756B2uspto-grants-2012_08