Réaction #217176

ord-39f35173d1c540c78777ecc896a9c787

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
CC(C)(C)CC(=O)Cl
3,3-dimethylbutyryl chloride
→
CCOC(=O)CCNC(=O)[C@@H](Cc1c[nH]c2ccccc12)NC(=O)[C@H](CC(C)C)NC(=O)CC(C)(C)C
product
CCOC(=O)CCNC(=O)[C@@H](Cc1c[nH]c2ccccc12)NC(=O)[C@H](CC(C)C)NC(=O)CC(C)(C)C
N-[N-[N-(3,3-dimethylbutyryl)-L-leu-cyl]-D-tryptophanyl]-β-alanine ethyl ester

Réactifs

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
CC(C)(C)CC(=O)Cl
3,3-dimethylbutyryl chloride

Réactifs

Aucun

Solvants

c1ccncc1
pyridine

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Autrequenched with water (0.1 ml)
  2. 2
    Concentrationconcentrated under reduced pressure
  3. 3
    AutreThe residue was purified by preparative TLC (Merck, Kieselgel 60 F254) with chloroform/methanol=15/1 for development

Mode opératoire

To a solution of Leu-DTrp-βAla-OEt.TFA (33.0 mg) obtained in Example 51-(1) in pyridine (0.5 ml) was added 3,3-dimethylbutyryl chloride (12.8 ml) at 0° C. under nitrogen. The reaction mixture was stirred for 10 min, quenched with water (0.1 ml), and concentrated under reduced pressure. The residue was purified by preparative TLC (Merck, Kieselgel 60 F254) with chloroform/methanol=15/1 for development to give the product (21.8 mg).

Source

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