Sodium Thiosulfate → HCID 90370256, compound

HRID 2175986Notes

Reaction equation

HRID 2175986 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([CH3:14])[C:5](=[O:13])[CH2:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)([O-])O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl>[CH3:14][N:4]([CH2:3][CH:2]=[O:1])[C:5](=[O:13])[CH2:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 60740715HCID 60740715, compound

Product 1

HCID 90370256HCID 90370256, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 11.9 g of ethyl 4-[(2-hydroxyethyl)(methyl)amino]-4-oxobutanoate and 120 mL of methylene chloride was added slowly 26.0 g of Dess-Martin Periodinane under ice cooling, and the mixture was allowed to warm to room temperature over 3 hours. An aqueous sodium hydrogen carbonate solution and an aqueous sodium thiosulfate solution were added to the reaction mixture, followed by stirring for 30 minutes at room temperature. An aqueous layer was extracted with methylene chloride, the organic layers were combined and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:4), thereby obtaining 4.48 g of ethyl 4-[methyl(2-oxoethyl)amino]-4-oxobutanoate.

Workup

  1. extractionAn aqueous layer was extracted with methylene chloride
  2. dry with materialdried over anhydrous sodium sulfate
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:4)

Sources & evidence

ORD record
ord-51ae9ac58f4447b39a9345bc87455cd8
Source dataset
uspto-grants-2015_06
Patent number
US09062032B2

Reaction notes

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