Reacción #41383

Ecuación de reacción

(2S)-2-[(tert-butoxycarbonyl)amino]pentanoic acid

N,O-dimethylhydroxylamine hydrochloride

O-benzotriazole-1-yl-N,N,N′,N′-tetramethyl-uronium hexafluorophosphate

N,N-diisopropylethylamine

→

(S)-tert-butyl 1-(methoxy(methyl)amino)-1-oxopentan-2-ylcarbamate

Disolventes

DMF

ethyl acetate

water

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe mixture was shaken
2. 2
   Otrothe layers separated
3. 3
   Lavadothe water layer washed twice with ethyl acetate
4. 4
   LavadoThe collected organic phase was washed with a small portion of water
5. 5
   Secadodried over sodium sulphate
6. 6
   OtroThe solvent was removed
7. 7
   Otrothe crude product was purified by flash chromatography

Procedimiento

Commercially available (2S)-2-[(tert-butoxycarbonyl)amino]pentanoic acid (1.0 g, 4.6 mmol) and N,O-dimethylhydroxylamine hydrochloride (0.47 g, 4.8 mmol) were dissolved in DMF (18 ml). O-benzotriazole-1-yl-N,N,N′,N′-tetramethyl-uronium hexafluorophosphate (1.92 g, 5.06 mmol) and N,N-diisopropylethylamine (2.47 ml, 14.5 mmol) were added. The reaction was stirred at r.t. over night. The reaction was poured into a mixture of water and ethyl acetate. The mixture was shaken, the layers separated and the water layer washed twice with ethyl acetate. The collected organic phase was washed with a small portion of water and dried over sodium sulphate. The solvent was removed under educed pressure and the crude product was purified by flash chromatography.

Fuente