Reacción #651868

ord-6019bc181b3340fa8a2e98dfe173d118

Ecuación de reacción

COc1cc(C)c(S(=O)(=O)NC(=N)NCCC[C@@H]2NC(=O)[C@@H](C(C)C)NC(=O)[C@H](Cc3ccccc3)NC(=O)[C@H](CC(=O)O)NC(=O)CCNC2=O)c(C)c1C
cyclo-(Arg(Mtr)-β-Ala-Asp-Phe-D-Val)
→
CC(C)[C@H]1NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@H](CC(=O)O)NC(=O)CCNC(=O)[C@H](CCCNC(=N)N)NC1=O
cyclo-(Arg-β-Ala-Asp-Phe-D-Val)

Reactantes

COc1cc(C)c(S(=O)(=O)NC(=N)NCCC[C@@H]2NC(=O)[C@@H](C(C)C)NC(=O)[C@H](Cc3ccccc3)NC(=O)[C@H](CC(=O)O)NC(=O)CCNC2=O)c(C)c1C
cyclo-(Arg(Mtr)-β-Ala-Asp-Phe-D-Val)

Reactivos

Ninguno

Disolventes

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

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Concentraciónconcentrated
  2. 2
    workup.ADDITIONafter diluting with water
  3. 3
    Otrofreeze-dried
  4. 4
    FiltraciónGel filtration
  5. 5
    Otroon Sephadex G 10 (acetic acid/water 1:1) and subsequent purification by preparative HPLC under the conditions

Procedimiento

A solution of 0.28 g of cyclo-(Arg(Mtr)-β-Ala-Asp-Phe-D-Val) [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, after diluting with water, 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-β-Ala-Asp-Phe-D-Val); RT=17.0; M+ 589.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US06169072Auspto-grants-2001_01