Reacción #59270

Ecuación de reacción

hydrogen chloride

sodium hydride

((S)-6-Oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)-carbamic acid tert-butyl ester

methyl bromoacetate

→

oil

Rendimiento 63.0%

((S)-7-tert.-Butoxycarbonylamino-6-oxo-6,7-dihydro-dibenzo[b,d]azepin-5-yl)-acetic acid methyl ester

Rendimiento 63.0%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe solution stirred for another 6 h
2. 2
   Extracciónextracted with ethyl acetate (10 ml)
3. 3
   ExtracciónAfter back-extraction of the aqueous phases with ethyl acetate
4. 4
   Lavadothe combined organic phases were washed with water and saturated aqueous sodium chloride
5. 5
   Secadodried over magnesium sulfate
6. 6
   Otroevaporated to dryness

Procedimiento

((S)-6-Oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)-carbamic acid tert-butyl ester (284 mg, 0.88 mmol) were diluted in DMF (5 ml) and treated with sodium hydride (60 mg of 60% suspension in mineral oil, 1.5 mmol). After stirring for 30 minutes, methyl bromoacetate (0.14 ml, 1.5 mmol) were added and the solution stirred for another 6 h. The pH is adjusted to 1.5 with 2N hydrogen chloride and extracted with ethyl acetate (10 ml). After back-extraction of the aqueous phases with ethyl acetate, the combined organic phases were washed with water and saturated aqueous sodium chloride, dried over magnesium sulfate and evaporated to dryness. After chromatography (silica, eluent cyclohexane/ethyl acetate 88/12), the product was obtained as off-white viscous oil (63%); MS: m/e=397(M+H+).

Fuente