Réaction #217177

ord-de5992a38fdb48f288f21e3b7c34d3a1

Équation de réaction

CCOC(=O)CCNC(=O)[C@@H](Cc1c[nH]c2ccccc12)NC(=O)[C@@H](N)CC(C)C.O=C(O)C(F)(F)F
Leu-DTrp-βAla-OEt-TFA
O=C=Nc1ccccc1
phenyl isocyanate
→
CCOC(=O)CCNC(=O)[C@@H](Cc1c[nH]c2ccccc12)NC(=O)[C@H](CC(C)C)NC(=O)Nc1ccccc1
product
CCOC(=O)CCNC(=O)[C@@H](Cc1c[nH]c2ccccc12)NC(=O)[C@H](CC(C)C)NC(=O)Nc1ccccc1
PhNHCO-Leu-DTrp-βAla-OEt

Réactifs

—
TEA
CCOC(=O)CCNC(=O)[C@@H](Cc1c[nH]c2ccccc12)NC(=O)[C@@H](N)CC(C)C.O=C(O)C(F)(F)F
Leu-DTrp-βAla-OEt-TFA
O=C=Nc1ccccc1
phenyl isocyanate

Réactifs

Aucun

Solvants

ClC(Cl)Cl
chloroform

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Concentrationconcentrated under reduced pressure
  2. 2
    AutreThe residue was purified
  3. 3
    Séchageby dry column flash chromatography (Merck, Kieselgel 60) with chloroform/methanol=10/1
  4. 4
    Lavagefor elution

Mode opératoire

To a solution of Leu-DTrp-βAla-OEt-TFA (40.6 mg) obtained in Example 51-(1) in chloroform (2 ml) were added TEA (20 μl) and phenyl isocyanate (15 μl) at room temperature under nitrogen. The reaction mixture was stirred for 1 h, and concentrated under reduced pressure. The residue was purified by dry column flash chromatography (Merck, Kieselgel 60) with chloroform/methanol=10/1 for elution to give the product (39.6 mg).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US05470833uspto-grants-1995_11