Reacción #87110

Ecuación de reacción

isobutylchloroformate

dimethylhydroxylamine

dimethylhydroxylamine hydrochloride

triethylamine

N-methylmorpholine

(S)-2-((tert-butoxycarbonyl)amino)-3-cyclohexylpropanoic acid

→

(S)-tert-Butyl (3-cyclohexyl-1-(methoxy(methyl)amino)-1-oxopropan-2-yl)carbamate

Rendimiento 105.2%

Disolventes

DCM

DCM

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowas quenched with water
2. 2
   Lavadowashed with sodium bicarbonate (sat.)
3. 3
   Extracciónextracted with EtOAc (2×)
4. 4
   Lavadowashed with brine
5. 5
   Secadodried with sodium sulfate
6. 6
   Filtraciónfiltered
7. 7
   Concentraciónconcentrated

Procedimiento

To a solution of dimethylhydroxylamine hydrochloride (3.98 g, 40.6 mmol) in DCM (50 mL) at 0° C. was added triethylamine (5.43 mL, 41.9 mmol). In a separate flask (S)-2-((tert-butoxycarbonyl)amino)-3-cyclohexylpropanoic acid (10.0 g, 36.9 mmol) in DCM (50 mL) and THF (50 mL) was cooled to 0° C. and isobutylchloroformate (4.83 mL, 36.9 mmol) was added followed by N-methylmorpholine (4.06 mL, 36.9 mmol). After 1 h it was added to the dimethylhydroxylamine mixture. The combined mixture was allowed to warm to ambient temperature over 16 h at which time it was quenched with water, washed with sodium bicarbonate (sat.), extracted with EtOAc (2×), washed with brine, dried with sodium sulfate, filtered, and concentrated. (S)-tert-Butyl (3-cyclohexyl-1-(methoxy(methyl)amino)-1-oxopropan-2-yl)carbamate (12.2 g) was provided as a colorless oil that was carried forward without further purification. MS (EI) for C16H30N2O4, found 215.3 [M-Boc]+.

Fuente