Reacción #440774

ord-d384f96e20dc42f5b16417e8184612c1

Ecuación de reacción

N[C@@H](CC(=O)O)C(=O)O
Asp
CN(C)C(On1nnc2ccccc21)=[N+](C)C.F[B-](F)(F)F.On1nnc2ccccc21
HOBT TBTU
CCN(CC(=O)N[C@@H](CC(=O)OCc1ccccc1)C(=O)O)C(=O)OC(C)(C)C
BOC-N(Et)Gly-(L)-Asp(OBzl)—OH
→
CCN(CC(=O)N[C@@H](CC(=O)OCc1ccccc1)C(=O)N[C@@H](CC1CCCCC1)C(N)=O)C(=O)OC(C)(C)C
BOC-N(Et)Gly-(L)-Asp(OBzl)-(L)-Cha-NH2

Reactantes

—
1.77A
N[C@@H](CC(=O)O)C(=O)O
Asp
CN(C)C(On1nnc2ccccc21)=[N+](C)C.F[B-](F)(F)F.On1nnc2ccccc21
HOBT TBTU
CCN(CC(=O)N[C@@H](CC(=O)OCc1ccccc1)C(=O)O)C(=O)OC(C)(C)C
BOC-N(Et)Gly-(L)-Asp(OBzl)—OH

Reactivos

Ninguno

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Procedimiento

As a specific example of the HOBT/TBTU Method, when the general procedure is followed, 10 g (24.5 mmole) of BOC-N(Et)Gly-(L)-Asp(OBzl)—OH is used, then 9.3 g of BOC-N(Et)Gly-(L)-Asp(OBzl)-(L)-Cha-NH2 is prepared (96.1 A % pure, 1.77A % diastereomer at Asp), a 67.7% theoretical yield.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US06753409B1uspto-grants-2004_06