Reacción #642204

ord-a03691d193904cab9e673c65e099d5cd

Ecuación de reacción

CC(C)(C)OC(=O)N[C@@H](CCCNC(=N)N)C(=O)O
Boc-L-Arg-OH
Cl.N[C@@H](Cc1c[nH]c2ccccc12)C(=O)OCc1ccccc1
H-L-Trp-OBzl hydrochloride
On1nnc2ccccc21
HOBt
CCN(C(C)C)C(C)C
DIPEA
CN(C)C(On1nnc2ccccc21)=[N+](C)C.F[P-](F)(F)(F)(F)F
HBTU
CC(C)(C)OC(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)OCc1ccccc1
yellowish solid
Rendimiento 123.5%
CC(C)(C)OC(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)OCc1ccccc1
Boc-L-Arg-L-Trp-OBzl
Rendimiento 123.5%

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroEvaporation

Procedimiento

To a stirred solution of Boc-L-Arg-OH (792 mg, 2.75 mmoles), H-L-Trp-OBzl hydrochloride (832 mg, 2.5 mmoles), HOBt (1378 mg, 9 mmoles) and DIPEA (2.05 ml, 12 mmoles) in DMF (6 ml) and dichloromethane (3 ml) cooled on ice was added HBTU (1138 mg, 3 mmoles) in small portions over 10 minutes. The mixture was stirred on ice for 45 minutes and at room temperature for 45 minutes. Workup was performed as described for KP-2-1. Evaporation afforded 1.7 g of a yellowish solid.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08048852B2uspto-grants-2011_11