Reaction #1543045

ord-136df2ed25e84913898aa712a571fdc6

Reaction equation

NC(N)=NCCC[C@@H](N)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N1CCC[C@H]1C(=O)N1C[C@H](O)C[C@H]1C(=O)NCC(=O)N[C@@H](Cc1cccs1)C(=O)N[C@@H](CO)C(=O)N1Cc2ccccc2C[C@@H]1C(=O)N(CC(=O)N[C@@H](CCCN=C(N)N)C(=O)O)C1CCCCC1
CP-0597
→
CCC(=O)N(c1ccccc1)C1CCN(CCc2ccccc2)CC1.NC(N)=NCCC[C@@H](N)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N1CCC[C@H]1C(=O)N1C[C@H](O)C[C@H]1C(=O)NCC(=O)N[C@@H](Cc1cccs1)C(=O)N[C@@H](CO)C(=O)N1Cc2ccccc2C[C@@H]1C(=O)N(CC(=O)N[C@@H](CCCN=C(N)N)C(=O)O)C1CCCCC1
fentanyl CP-0597

Reactants

NC(N)=NCCC[C@@H](N)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N1CCC[C@H]1C(=O)N1C[C@H](O)C[C@H]1C(=O)NCC(=O)N[C@@H](Cc1cccs1)C(=O)N[C@@H](CO)C(=O)N1Cc2ccccc2C[C@@H]1C(=O)N(CC(=O)N[C@@H](CCCN=C(N)N)C(=O)O)C1CCCCC1
CP-0597
—
crude material

Reagents

None

Solvents

CC(=O)O.O
acetic acid H2O

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherpurified on RP-HPLC (90:10 to 35:65, H2O:CH3CN+0.1% TFA over 55 minutes) The desired fractions
  2. 2
    Otherevaporated

Procedure

This heterodimer of Isomer A from Example XI and CP-0597 was prepared by a similar coupling procedure as described in Example IV. The crude material was dissolved into 10% acetic acid/H2O and purified on RP-HPLC (90:10 to 35:65, H2O:CH3CN+0.1% TFA over 55 minutes) The desired fractions were combined, evaporated and lyophilized to give 18.4 mg of the fentanyl-CP-0597 heterodimer CP-0880 as a white powder.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05843900uspto-grants-1998_12