반응 #934502

반응 방정식

potassium carbonate

t-butyl [(S)-α-[[(S)-1-[[(1S,2S,4S)-6-amino-1-(cyclohexylmethyl)-2-hydroxy-4-isopropylhexyl]carbamoyl]-2-imidazol-4-ylethyl]carbamoyl]phenethyl]carbamate hydrochloride

benzyl [(methylthio)formimidoyl]carbamate

Hunig base

→

benzyl [N-[(3S,5S,6S)-6-[[N-[N-(t-butoxycarbonyl)-3-phenyl-L-alanyl]-L-histidyl]amino]-7-cyclohexyl-5-hydroxy-3-isopropylheptyl]amidino]carbamate

수율 80.0%

용매

ethanol

반응 조건

후처리

1. 1
   온도Thereafter, the reaction mixture is cooled
2. 2
   추출extracted with methylene chloride
3. 3
   건조The methylene chloride extracts are dried over magnesium sulphate
4. 4
   기타evaporated under reduced pressure
5. 5
   기타Chromatography of the residue obtained on 2 g of silica gel with a mixture of methylene chloride and isopropanol as the eluting agent

실험 절차

0.136 g (0.197 mmol) of t-butyl [(S)-α-[[(S)-1-[[(1S,2S,4S)-6-amino-1-(cyclohexylmethyl)-2-hydroxy-4-isopropylhexyl]carbamoyl]-2-imidazol-4-ylethyl]carbamoyl]phenethyl]carbamate hydrochloride, 0.051 g (0.2 mmol) of benzyl [(methylthio)formimidoyl]carbamate and 0.07 ml (0.34 mmol) of Hunig base in 1 ml of absolute ethanol are stirred at 70° under argon for 3 hours. Thereafter, the reaction mixture is cooled, poured into 2N potassium carbonate solution and extracted with methylene chloride. The methylene chloride extracts are dried over magnesium sulphate and evaporated under reduced pressure. Chromatography of the residue obtained on 2 g of silica gel with a mixture of methylene chloride and isopropanol as the eluting agent yields 0.131 g of benzyl [N-[(3S,5S,6S)-6-[[N-[N-(t-butoxycarbonyl)-3-phenyl-L-alanyl]-L-histidyl]amino]-7-cyclohexyl-5-hydroxy-3-isopropylheptyl]amidino]carbamate as a colourless oil, MS: 831 (M+H)+.

출처