HCID 22407001, compound → HCID 22406996, compound

HRID 440337Notes

Reaction equation

HRID 440337 reaction equation
CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.[OH:14][CH:15]([C:21]1[S:22][C:23]([S:26]([NH2:29])(=[O:28])=[O:27])=[CH:24][N:25]=1)[CH2:16][O:17][CH2:18][O:19][CH3:20]>CC(C)=O>[CH3:20][O:19][CH2:18][O:17][CH2:16][C:15]([C:21]1[S:22][C:23]([S:26]([NH2:29])(=[O:28])=[O:27])=[CH:24][N:25]=1)=[O:14]

Participants

4

Reactant 2

HCID 22407001HCID 22407001, compoundHCID 131709961Jones' reagent

Product 1

HCID 22406996HCID 22406996, compoundYield 5.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Jones' reagent (0.14 mL, 0.39 mmol, 2.67M) was added dropwise to a 0° C. solution of 2-(1-hydroxy-2-(methoxymethoxy)ethyl)-5-thiazole sulfonamide (0.086 g, 0.32 mmol) in acetone (1 mL). The ice bath was removed and the solution stirred for 15 min. The reaction was incomplete an additional 0.07 mL of Jones' reagent was added and the reaction stirred for 15 more minutes. The reaction was quenched with a few drops of isopropanol and the acetone removed in vacuo. The residue was taken up in water and extracted with EtOAc. The combined extracts were dried (MgSO4), concentrated and purified by flash chromatography using 55% EtOAc/hexane to give 4.8 mg (5.3%) of 2-(2-(methoxymethoxy)ethanoyl)-5-thiazole sulfonamide.

Workup

  1. customThe ice bath was removed
  2. additionwas added
  3. stirringthe reaction stirred for 15 more minutes
  4. customThe reaction was quenched with a few drops of isopropanol
  5. customthe acetone removed in vacuo
  6. extractionextracted with EtOAc
  7. dry with materialThe combined extracts were dried (MgSO4)
  8. concentrationconcentrated
  9. custompurified by flash chromatography

Sources & evidence

ORD record
ord-a6094f8d573d43cc8915c6b82164a422
Source dataset
uspto-grants-1996_05
Patent number
US05519040

Reaction notes

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