Water → HCID 86752099, compound

HRID 863264Notes

Reaction equation

HRID 863264 reaction equation
[CH2:1]([NH:5][C:6](=[O:30])[C@H:7]([CH3:29])[CH2:8][C@@H:9]1[O:13][C:12]([CH3:15])([CH3:14])[N:11]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@H:10]1[CH2:23][C@H:24]([CH3:28])[CH2:25][CH2:26][OH:27])[CH2:2][CH2:3][CH3:4].[Na].[OH2:32]>C(Cl)(Cl)(Cl)Cl.C(#N)C.C(Cl)Cl.C(O)(C)C.O.[Ru](Cl)(Cl)Cl>[CH2:1]([NH:5][C:6](=[O:30])[C@H:7]([CH3:29])[CH2:8][C@@H:9]1[O:13][C:12]([CH3:15])([CH3:14])[N:11]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[C@H:10]1[CH2:23][C@H:24]([CH3:28])[CH2:25][C:26]([OH:32])=[O:27])[CH2:2][CH2:3][CH3:4]

Participants

9

Reactant 3

HCID 962WaterHCID 5360545SodiumHCID 86752100HCID 86752100, compound

Product 1

HCID 86752099HCID 86752099, compound

Reagents, catalysts & solvents 5

HCID 6093376Ruthenium trichloride hydrateCatalystHCID 3776IsopropanolSolventHCID 5943Carbon TetrachlorideSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 311 mg of 3-[N-tert-butoxycarbonyl-4(S)-[4-hydroxy-2(S)-methylbutyl]-2,2-dimethyl-1,3-oxazolidin-5(S)-yl]-2-(R)-methyl-propionic acid (N-butyl)amide in a mixture of 4.8 ml of carbon tetrachloride and 4.8 ml of acetonitrile is added to a mixture of 928 mg of sodium metaperiodidate, 19 mg of ruthenium(III) chloride hydrate and 0.6 ml of water while stirring vigorously. After 1 h, the mixture is diluted with 30 ml of methylene chloride and 5 ml of isopropanol, and the aqueous phase is separated off and extracted with methylene chloride. The combined organic phase is concentrated, the residue is taken up in 10 ml of toluene and the mixture is concentrated again. The dark-coloured residue is purified by FC over 25 g of silica gel with a 50:50:1 mixture of hexane, ethyl acetate and glacial acetic acid: Rf (B)=0.18; FAB-MS: (M+H)+ =443.

Workup

  1. customthe aqueous phase is separated off
  2. extractionextracted with methylene chloride
  3. concentrationThe combined organic phase is concentrated
  4. concentrationthe mixture is concentrated again
  5. customThe dark-coloured residue is purified by FC over 25 g of silica gel with a 50:50:1 mixture of hexane, ethyl acetate and glacial acetic acid

Sources & evidence

ORD record
ord-f03b954565b24a79a672cac287619f8f
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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