반응 #82350

반응 방정식

N2 [3(S)-(benzyloxyformamido)-4-(4-tert.butoxyphenyl)-2(R)-hydroxybutyl]-N1 -tert.butyl-L-prolinamide

N-(benzyloxycarbonyl)-L-asparagine

→

N2 [3(S)-[[N-(benzyloxycarbonyl)-L-asparaginyl]amino]-4-(4-tert.butoxyphenyl)-2(R)-hydroxybutyl]-N1 -tert.butyl-L-prolinamide

수율 31.1%

용매

ethanol

반응 조건

후처리

1. 1
   기타The catalyst was removed by filtration
2. 2
   기타the filtrate was evaporated
3. 3
   기타to give an oil which
4. 4
   기타The crude product was chromatographed on a column of silica gel using 10% methanol in dichloromethane for the elution

실험 절차

A solution of 1.58 g of N2 -[3(S)-(benzyloxyformamido)-4-(4-tert.butoxyphenyl)-2(R)-hydroxybutyl]-N1 -tert.butyl-L-prolinamide in 200 ml of ethanol was hydrogenated over 100 mg of 10% palladium-on-carbon for 4 hours. The catalyst was removed by filtration and the filtrate was evaporated to give an oil which was coupled with 0.74 g of N-(benzyloxycarbonyl)-L-asparagine in a manner analogous to that described in Example 1. The crude product was chromatographed on a column of silica gel using 10% methanol in dichloromethane for the elution. There was obtained 0.59 g of N2 -[3(S)-[[N-(benzyloxycarbonyl)-L-asparaginyl]amino]-4-(4-tert.butoxyphenyl)-2(R)-hydroxybutyl]-N1 -tert.butyl-L-prolinamide as a white solid; MS: m/e 654 [M+H]+.

출처