Reaction #969876

ord-0b684c819b1449a88100176c90eb6a4f

Reaction equation

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
Yield 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
Yield 50.0%

Reactants

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

Reagents

None

Solvents

CN(C)C=O
dimethylformamide

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

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

Procedure

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.v1Patent: US08236756B2uspto-grants-2012_08