Reaktion #59270

Reaktionsgleichung

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

Ausbeute 63.0%

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

Ausbeute 63.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

((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+).

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