Reacción #2057685

ord-f5e6293cdb4d4c4982f77797c7679172

Ecuación de reacción

CC(C)(C)OC(=O)CC[C@H](NC(=O)OCc1ccccc1)C(=O)O
(S)-2-Benzyloxycarbonylamino-pentanedioic acid 5-tert-butyl ester
CCCCOC(=O)N1CCNCC1
piperazine-1-carboxylic acid butyl ester
CCN1CCOCC1
N-ethylmorpholine
CCOC(=O)C(C#N)=NOC(N(C)C)=[N+](C)C.F[B-](F)(F)F
TOTU
→
CCCCOC(=O)N1CCN(C(=O)[C@H](CCC(=O)OC(C)(C)C)NC(=O)OCc2ccccc2)CC1
crude product
CCCCOC(=O)N1CCN(C(=O)[C@H](CCC(=O)OC(C)(C)C)NC(=O)OCc2ccccc2)CC1
4-((S)-2-Benzyloxycarbonylamino-4-tert-butoxycarbonyl-butyryl)-piperazine-1-carboxylic acid butyl ester

Reactantes

CC(C)(C)OC(=O)CC[C@H](NC(=O)OCc1ccccc1)C(=O)O
(S)-2-Benzyloxycarbonylamino-pentanedioic acid 5-tert-butyl ester
CCCCOC(=O)N1CCNCC1
piperazine-1-carboxylic acid butyl ester
CCN1CCOCC1
N-ethylmorpholine
CCOC(=O)C(C#N)=NOC(N(C)C)=[N+](C)C.F[B-](F)(F)F
TOTU

Reactivos

Ninguno

Disolventes

CCOC(C)=O
ethyl acetate
CN(C)C=O
DMF

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Lavadosubsequently washed with aqueous LiCl (4%) and saturated NaHCO3

Procedimiento

To a solution of 9.06 g (S)-2-Benzyloxycarbonylamino-pentanedioic acid 5-tert-butyl ester in 100 ml DMF were added 5.00 g piperazine-1-carboxylic acid butyl ester hydrotrifluoroacetate, 13.7 ml N-ethylmorpholine and 8.8 g TOTU. After stirring for 12 h the solution was diluted with ethyl acetate and subsequently washed with aqueous LiCl (4%) and saturated NaHCO3. The crude product obtained after evaporation of the solvent was used without further purification. Yield: 15.8 g.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08426420B2uspto-grants-2013_04