Sodium Hydroxide → Di-tert-butyl (2R,3R)-2-hydroxy-3-{[5-oxido-4-(phenylsulphonyl)-1,2,5-oxadiazol-3-yl]-oxy}-succinate

HRID 1013433Notes

Reaction equation

HRID 1013433 reaction equation
[OH-].[Na+].[C:3]1([S:9]([C:12]2[C:16](S(C3C=CC=CC=3)(=O)=O)=[N:15][O:14][N+:13]=2[O-:26])(=[O:11])=[O:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:27]([CH:34]([CH:36]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[OH:37])[OH:35])([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28]>C1COCC1>[OH:37][C@H:36]([C@@H:34]([O:35][C:16]1[C:12]([S:9]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)(=[O:10])=[O:11])=[N+:13]([O-:26])[O:14][N:15]=1)[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:38]([O:40][C:41]([CH3:42])([CH3:43])[CH3:44])=[O:39]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 281630Di-tert-butyl tartrateHCID 124054663,4-Di(benzenesulfonyl)-2-oxo-1,2,5lambda~5~-oxadiazole

Product 1

HCID 67316492Di-tert-butyl (2R,3R)-2-hydroxy-3-{[5-oxido-4-(phenylsulphonyl)-1,2,5-oxadiazol-3-yl]-oxy}-succinate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

50% NaOH solution (1.2 g-30 mmol) is added in the course of ½ hour to a solution of 3,4-bis(phenylsulphonyl)-1,2,5-oxadiazole 2-oxide (7 g-19 mmol) and di-tert-butyl tartrate (5 g-19 mmol) in 100 ml of anhydrous THF. After stirring for 5 hours, the solvent is evaporated off to dryness and the residue is taken up in water and ethyl acetate. The organic fraction is dried with Na2SO4 and evaporated to dryness and subsequently purified by flash chromatography, using a (98:2) dichloromethane/ethanol mixture as eluant, to yield the expected product in the form of a colourless oil.

Workup

  1. customthe solvent is evaporated off to dryness
  2. dry with materialThe organic fraction is dried with Na2SO4
  3. customevaporated to dryness
  4. customsubsequently purified by flash chromatography

Sources & evidence

ORD record
ord-a19f08ad42c346d288993ad217c62249
Source dataset
uspto-grants-2011_07
Patent number
US07981920B2

Reaction notes

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