Sulfur Dioxide → HCID 19433999, compound

HRID 1736030Notes

Reaction equation

HRID 1736030 reaction equation
[N:1]1([CH2:7][CH2:8][N:9]2[C:14]([CH2:15][OH:16])=[CH:13][C:12]3[CH:17]=[CH:18][S:19][C:11]=3[S:10]2(=[O:21])=[O:20])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C([Li])CCC.[S:27](=[O:29])=[O:28].[NH2:30]OS(O)(=O)=O.C([O-])(=O)C.[Na+]>C1COCC1>[OH:16][CH2:15][C:14]1[N:9]([CH2:8][CH2:7][N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)[S:10](=[O:20])(=[O:21])[C:11]2[S:19][C:18]([S:27]([NH2:30])(=[O:29])=[O:28])=[CH:17][C:12]=2[CH:13]=1

Participants

7

Reactant 5

HCID 1119Sulfur DioxideHCID 76284hydroxylamine-O-sulfonic acidHCID 517045Sodium AcetateHCID 19434112HCID 19434112, compoundHCID 178418339Butyllithium

Product 1

HCID 19433999HCID 19433999, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of the product from Step D (3.25 g, 9.85 mmol) in anhydrous THF (40 mL) under nitrogen at -70° C. was added n-butyllithium (2.5M in hexanes, 9.06 mL, 22.7 mmol). The mixture was stirred for 7 min before sulfur dioxide gas was passed over the solution for about 5 min. The resulting mixture was warmed to ambient temperature and evaporated to a residue which was mixed with ice-water (150 mL), hydroxylamine-O-sulfonic acid (3.34 g, 29.6 mmol) and sodium acetate (6.20 g, 45.6 g) and stirred for 4 h at ambient temperature. The reaction mixture was extracted with ethyl acetate (2×100 mL) and the combined extracts were dried over magnesium sulfate and evaporated to a residue which was purified by column chromatography (silica, 5% to 10% methanol/methylene chloride) to give a glass (3.10 g, 77%).

Workup

  1. customevaporated to a residue which
  2. extractionThe reaction mixture was extracted with ethyl acetate (2×100 mL)
  3. dry with materialthe combined extracts were dried over magnesium sulfate
  4. customevaporated to a residue which
  5. customwas purified by column chromatography (silica, 5% to 10% methanol/methylene chloride)

Sources & evidence

ORD record
ord-43007841f19946ab8f3e792c58d4d1e6
Source dataset
uspto-grants-1996_07
Patent number
US05538966

Reaction notes

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