تفاعل #59270

معادلة التفاعل

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

المردود 63.0%

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

المردود 63.0%

المذيبات

DMF

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

((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+).

المصدر