Reaktion #82350

Reaktionsgleichung

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

Ausbeute 31.1%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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]+.

Quelle