Reacción #1767237

ord-fb7aa888e3624fb4bfcc6f83480217c2

Ecuación de reacción

C(=NC1CCCCC1)=NC1CCCCC1
DCCI
CC(C)(C)OC(=O)CC[C@H](NC(=O)OCc1ccccc1)C(=O)O
Z-Glu(OtBU)-OH
On1nnc2ccccc21
HOBt
CC(C)C[C@H](NC(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CCCCNC(=O)OC(C)(C)C)[C@@H](C)O)C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](CC(C)C)C(=O)OC(C)(C)C)[C@@H](C)O)C(C)C
H-Lys(Boc)-Ser-Gln-Thr-Pro-Leu-Val-Thr-Leu-OtBu
→
CC(C)C[C@H](NC(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CCCCNC(=O)OC(C)(C)C)NC(=O)[C@H](CCC(=O)OC(C)(C)C)NC(=O)OCc1ccccc1)[C@@H](C)O)C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](CC(C)C)C(=O)OC(C)(C)C)[C@@H](C)O)C(C)C
Z-Glu(OtBu)-Lys(Boc)-Ser-Gln-Thr-Pro-Leu-Val-Thr-Leu-OtBu

Reactantes

C(=NC1CCCCC1)=NC1CCCCC1
DCCI
CC(C)(C)OC(=O)CC[C@H](NC(=O)OCc1ccccc1)C(=O)O
Z-Glu(OtBU)-OH
On1nnc2ccccc21
HOBt
CC(C)C[C@H](NC(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CCCCNC(=O)OC(C)(C)C)[C@@H](C)O)C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](CC(C)C)C(=O)OC(C)(C)C)[C@@H](C)O)C(C)C
H-Lys(Boc)-Ser-Gln-Thr-Pro-Leu-Val-Thr-Leu-OtBu

Reactivos

Ninguno

Disolventes

CN(C)C=O
DMF
CN(C)C=O
DMF

Condiciones de reacción

Temperatura
-22°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    workup.ADDITIONare added to the solution
  2. 2
    Filtraciónthe DCHU is filtered out
  3. 3
    Otrothe filtrate is evaporated to dryness

Procedimiento

843 mg Z-Glu(OtBU)-OH and 676 mg HOBt are dissolved in 10 ml DMF. After cooling to -22° C., 2.82 g H-Lys(Boc)-Ser-Gln-Thr-Pro-Leu-Val-Thr-Leu-OtBu (Example VII.2) and 517 mg DCCI, dissolved in 2 ml DMF, are added to the solution. After stirring at -22° C. for some time, the DCHU is filtered out and the filtrate is evaporated to dryness.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US04271152uspto-grants-1981_06