Hydrogen Peroxide → HCID 66859765, compound

HRID 1888317Notes

Reaction equation

HRID 1888317 reaction equation
[F:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1([C@H:10]([OH:31])/[CH:11]=[CH:12]/[C@H:13]2[CH2:17][O:16][C:15](=[O:18])[N:14]2[CH2:19][CH2:20][S:21][C:22]2[S:23][CH:24]=[C:25]([C:27]([O:29][CH3:30])=[O:28])[N:26]=2)[CH2:9][CH2:8][CH2:7]1.FCCCCC1([C@H](O)/C=C/[C@H]2COC(=O)N2CCSC2SC=C(C(O)=O)N=2)CCC1.OO.[OH2:64].C[OH:66]>[O-][W]([O-])(=O)=O.[Na+].[Na+]>[F:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1([C@H:10]([OH:31])/[CH:11]=[CH:12]/[C@H:13]2[CH2:17][O:16][C:15](=[O:18])[N:14]2[CH2:19][CH2:20][S:21]([C:22]2[S:23][CH:24]=[C:25]([C:27]([O:29][CH3:30])=[O:28])[N:26]=2)(=[O:66])=[O:64])[CH2:9][CH2:8][CH2:7]1

Participants

7

Reactant 5

HCID 784Hydrogen PeroxideHCID 887MethanolHCID 962WaterHCID 11294085HCID 11294085, compoundHCID 68771292HCID 68771292, compound

Product 1

HCID 66859765HCID 66859765, compound

Reagents, catalysts & solvents 1

HCID 26052Sodium tungstateCatalyst

Procedure

To a solution of methyl 2-{[2-((4S)-4-{(1E,3R)-3-[1-(4-fluorobutyl)cyclobutyl]-3-hydroxy-1-propenyl}-2-oxo -1,3-oxazolidin-3-yl)ethyl]sulfanyl}-1,3-thiazole-4-carboxylate (methyl ester of compound 8-1) (78.0 mg) in methanol (1.0 mL) were added sodium tungstate(VI) dihydrate (14.0 mg) and 30% hydrogen peroxide solution (0.19 mL) at 0° C. and the solution was stirred for 1 Hour and then for 3 Hours at room temperature. Water was added to the reaction solution, which was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate and concentrated. The obtained residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=2:3) to give the title compound (70.4 mg) having the following physical data.

Workup

  1. customat room temperature
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe obtained residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=2:3)

Sources & evidence

ORD record
ord-7307c46bbf8143cc8f7367ad31c075a6
Source dataset
uspto-grants-2013_08
Patent number
US08501793B2

Reaction notes

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