반응 #59270

반응 방정식

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

수율 63.0%

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

수율 63.0%

용매

DMF

반응 조건

후처리

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

실험 절차

((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+).

출처