반응 #82370

반응 방정식

N2 [3(S)-[[N-(benzyloxycarbonyl)-3-(methylsulphinyl)-L-alanyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N1 -tert.butyl-L-prolinamide N2 -oxide

3-chloroperbenzoic acid

→

N2 [3(S)-[[N-(benzyloxycarbonyl)-3-(methylsulphonyl)-L-alanyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N1 -tert.butyl-L-prolinamide N2 -oxide monohydrate

수율 34.5%

용매

methanol

반응 조건

후처리

1. 1
   기타The solvent was removed by evaporation
2. 2
   기타the residue was partitioned between dichloromethane and 2M sodium hydroxide solution
3. 3
   기타The organic phase was evaporated
4. 4
   기타the residue was crystallized from ethyl acetate/n-hexane

실험 절차

A solution of 154 mg of N2 -[3(S)-[[N-(benzyloxycarbonyl)-3-(methylsulphinyl)-L-alanyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N1 -tert.butyl-L-prolinamide N2 -oxide (two diastereomers) in 5 ml of methanol was treated with 84 mg of 3-chloroperbenzoic acid and the solution was stirred at 20° C. for 16 hours. The solvent was removed by evaporation and the residue was partitioned between dichloromethane and 2M sodium hydroxide solution. The organic phase was evaporated and the residue was crystallized from ethyl acetate/n-hexane to give 28 mg of N2 -[3(S)-[[N-(benzyloxycarbonyl)-3-(methylsulphonyl)-L-alanyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N1 -tert.butyl-L-prolinamide N2 -oxide monohydrate; MS: m/e 633 [M+H]+.

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