Reacción #1269874

Ecuación de reacción

N,N-diisopropylethylamine

(2S)-2-amino-N-{(1R)-2-cyclobutyl-1-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}-3-phenylpropanamide

Boc-homophe-OH

TBTU

→

desired product

Rendimiento 85.0%

tert-Butyl [(1S)-1-({[(1S)-1-benzyl-2-({(1R)-2-cyclobutyl-1-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}amino)-2-oxoethyl]amino}carbonyl)-3-phenylpropyl]carbamate

Rendimiento 85.0%

Disolventes

N,N-dimethylformamide

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowas removed from the reaction mixture under vacuum
2. 2
   Otrothe resulting residue purified by preparative TLC in 40% EtOAc/Hexanes

Procedimiento

Into a 1-neck round-bottom flask was added (2S)-2-amino-N-{(1R)-2-cyclobutyl-1-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}-3-phenylpropanamide (217 mg, 0.511 mmol), Boc-homophe-OH (171 mg, 0.614 mmol), TBTU (246 mg, 0.767 mmol) and then N,N-dimethylformamide (14.5 mL, 0.187 mol) followed by N,N-diisopropylethylamine (0.187 mL, 1.07 mmol) dropwise at room temperature. The mixture was stirred at room temperature overnight The DMF was removed from the reaction mixture under vacuum and the resulting residue purified by preparative TLC in 40% EtOAc/Hexanes to give 298 mg (85% yield) of the desired product as a white solid.

Fuente