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 2256702Notes

Reaction equation

HRID 2256702 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-07fd5bbcefe54d128a9930793f31c86d
Source dataset
uspto-grants-1997_08
Patent number
US05654445

Reaction notes

Loading…