Reaction #452455

ord-53d747954d004fbbba3a335d5c7402ac

Reaction equation

COc1cc(C)c(S(=O)(=O)NC(=N)NCCC[C@@H]2NC(=O)[C@H]3CCCCN3C(=O)[C@@H](Cc3ccccc3)NC(=O)[C@H](CC(=O)O)NC(=O)CNC2=O)c(C)c1C
cyclo-(Arg(Mtr)-Gly-Asp-DPhe-DhPro)
→
N=C(N)NCCC[C@@H]1NC(=O)[C@H]2CCCCN2C(=O)[C@@H](Cc2ccccc2)NC(=O)[C@H](CC(=O)O)NC(=O)CNC1=O
cyclo-(Arg-Gly-Asp-DPhe-DhPro)

Reactants

COc1cc(C)c(S(=O)(=O)NC(=N)NCCC[C@@H]2NC(=O)[C@H]3CCCCN3C(=O)[C@@H](Cc3ccccc3)NC(=O)[C@H](CC(=O)O)NC(=O)CNC2=O)c(C)c1C
cyclo-(Arg(Mtr)-Gly-Asp-DPhe-DhPro)

Reagents

None

Solvents

Sc1ccccc1
thiophenol
O=C(O)C(F)(F)F
TFA
ClCCl
dichloromethane

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Concentrationconcentrated
  2. 2
    workup.ADDITIONthe residue is diluted with water
  3. 3
    Otherfreeze-dried
  4. 4
    FiltrationGel filtration
  5. 5
    Otheron Sephadex G 10 (acetic acid/water 1:1) and subsequent purification by preparative HPLC under the conditions

Procedure

A solution of 0.28 g of cyclo-(Arg(Mtr)-Gly-Asp-DPhe-DhPro) [obtainable by cyclization according to Ex. 1] in 8.4 ml of TFA, 1.7 ml of dichloromethane and 0.9 ml of thiophenol is allowed to stand at room temperature for 4 hours, then concentrated, and the residue is diluted with water and then freeze-dried. Gel filtration on Sephadex G 10 (acetic acid/water 1:1) and subsequent purification by preparative HPLC under the conditions indicated give cyclo-(Arg-Gly-Asp-DPhe-DhPro); FAB-MS (M+H): 587.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06127335uspto-grants-2000_10