反应 #59270

反应方程式

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

收率 63.0%

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

收率 63.0%

溶剂

DMF

反应条件

后处理

1. 1
   workup.STIRRINGthe solution stirred for another 6 h
2. 2
   萃取extracted with ethyl acetate (10 ml)
3. 3
   萃取After back-extraction of the aqueous phases with ethyl acetate
4. 4
   洗涤the combined organic phases were washed with water and saturated aqueous sodium chloride
5. 5
   干燥dried over magnesium sulfate
6. 6
   其他evaporated to dryness

实验过程

((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+).

来源