Methanol → N-Tert-butoxycarbonyl-2(R,S)-methyl-4(S)-hydroxy-5(S)-amino-7(S)-isopropyl-8-[3-(methylsulfonyl-methoxy)-4-tert-butyl-phenyl]-octanoic acid (N-butyl)amide

HRID 744790Notes

Reaction equation

HRID 744790 reaction equation
[OH:1][S:2]([O-:5])(=O)=O.OS(O[O-])(=O)=O.OS(O[O-])(=O)=O.[O-]S([O-])(=O)=O.[K+].[K+].[K+].[K+].[K+].[CH2:28]([NH:32][C:33](=[O:68])[CH:34]([CH3:67])[CH2:35][C@H:36]([OH:66])[C@@H:37]([NH:58][C:59]([O:61][C:62]([CH3:65])([CH3:64])[CH3:63])=[O:60])[CH2:38][C@@H:39]([CH:55]([CH3:57])[CH3:56])[CH2:40][C:41]1[CH:46]=[CH:45][C:44]([C:47]([CH3:50])([CH3:49])[CH3:48])=[C:43]([O:51][CH2:52]SC)[CH:42]=1)[CH2:29][CH2:30][CH3:31].[CH3:69]O>O>[CH2:28]([NH:32][C:33](=[O:68])[CH:34]([CH3:67])[CH2:35][C@H:36]([OH:66])[C@@H:37]([NH:58][C:59]([O:61][C:62]([CH3:63])([CH3:64])[CH3:65])=[O:60])[CH2:38][C@@H:39]([CH:55]([CH3:56])[CH3:57])[CH2:40][C:41]1[CH:46]=[CH:45][C:44]([C:47]([CH3:49])([CH3:48])[CH3:50])=[C:43]([O:51][CH2:52][S:2]([CH3:69])(=[O:5])=[O:1])[CH:42]=1)[CH2:29][CH2:30][CH3:31]

Participants

5

Reactant 3

HCID 887MethanolHCID 15793144Potassium caroateHCID 131719569N-Tert-butoxycarbonyl-2(R,S)-methyl-4(S)-hydroxy-5(S)-amino-7(S)-isopropyl-8-[3-(methylthio-methoxy)-4-tert-butyl-phenyl]-octanoic acid (N-butyl)amide

Product 1

HCID 131719570N-Tert-butoxycarbonyl-2(R,S)-methyl-4(S)-hydroxy-5(S)-amino-7(S)-isopropyl-8-[3-(methylsulfonyl-methoxy)-4-tert-butyl-phenyl]-octanoic acid (N-butyl)amide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

With stirring at 0° C., a solution of 115 mg of potassium monopersulfate triple salt in 0.5 ml of water is added dropwise to a solution of 74 mg of N-tert-butoxycarbonyl-2(R,S)-methyl-4(S)-hydroxy-5(S)-amino-7(S)-isopropyl-8-[3-(methylthio-methoxy)-4-tert-butyl-phenyl]-octanoic acid (N-butyl)amide in 0.5 ml of methanol and the mixture is then stirred at room temperature for a further 20 hours. The reaction mixture is partitioned between dichloromethane and water. The organic phases are concentrated by evaporation and the title compound is obtained from the residue by FC (11 g of silica gel, ethyl acetate/hexane=1:1): Rf (ethyl acetate/hexane=1:1)=0.26; FAB-MS (M+H)+ =627.

Workup

  1. stirringthe mixture is then stirred at room temperature for a further 20 hours
  2. customThe reaction mixture is partitioned between dichloromethane and water
  3. concentrationThe organic phases are concentrated by evaporation

Sources & evidence

ORD record
ord-7c6917a299c043ef8d9052418f42888b
Source dataset
uspto-grants-1996_09
Patent number
US05559111

Reaction notes

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