Reacción #1077579

Ecuación de reacción

N-tert-butoxycarbonyl-N-methyl-L-leucine

N,N-diisopropylethylamine

N,N-dimethylhydroxylamine hydrochloride salt

HBTU

→

desired product

(S)-[1-(Methoxy-methyl-carbamoyl)-3-methyl-butyl]-methyl-carbamic acid tert-butyl ester

Disolventes

EtOAc

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONtreated
2. 2
   Lavadowashed with saturated bicarbonate solution and brine
3. 3
   Secadodried over Na2SO4
4. 4
   Concentraciónconcentrated

Procedimiento

N-tert-butoxycarbonyl-N-methyl-L-leucine (5.0 g, 20.4 mmol) was dissolved in DMF (100 mL), treated with treated with N,N-diisopropylethylamine (28 mL, 163 mmol), N,N-dimethylhydroxylamine hydrochloride salt (2.0 g, 20.4 mmol), and HBTU (7.73 g, 20.4 mmol), then stirred overnight at room temperature. The reaction was diluted with EtOAc (500 mL), washed with saturated bicarbonate solution and brine, dried over Na2SO4, and concentrated to give the desired product as an oil; MS: 289.2 (M+1 for C14H28N2O4); TLC (SiO2) Rf 0.39 (8% MeOH/CH2Cl2), visualized with ninhydrin.

Fuente