Sulfur Dioxide → HCID 21480489, compound

HRID 1490055Notes

Reaction equation

HRID 1490055 reaction equation
CC1[N:6]2[CH2:7][C:8]3[N:9]([CH2:19][CH:5]2[CH2:4][O:3]1)[S:10](=[O:18])(=[O:17])[C:11]1[S:16][CH:15]=[CH:14][C:12]=1[CH:13]=3.C([Li])CCC.[S:25](=[O:27])=[O:26].[NH2:28]OS(O)(=O)=O>C1COCC1.CO.ClCCl>[OH:3][CH2:4][CH:5]1[CH2:19][N:9]2[S:10](=[O:18])(=[O:17])[C:11]3[S:16][C:15]([S:25]([NH2:28])(=[O:27])=[O:26])=[CH:14][C:12]=3[CH:13]=[C:8]2[CH2:7][NH:6]1

Participants

7

Reactant 4

HCID 1119Sulfur DioxideHCID 76284hydroxylamine-O-sulfonic acidHCID 21480486HCID 21480486, compoundHCID 178418339Butyllithium

Product 1

HCID 21480489HCID 21480489, compoundYield 6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

A solution of the product of Step G (1 g, 3.1 mmol) in THF (20 mL) at -78° C. was treated with 2.5M n-butyllithium (1.86 g, 4.65 mmol), sulfur dioxide, and hydroxylamine-O-sulfonic acid (1.05 g, 9.3 mmol) as described in Example 1, Step F to provide, after column chromatography (silica, methanol/dichloromethane, 1:9), the desired compound (70 mg, 6%) as an off-white solid: mp 170° C. dec.

Workup

  1. customto provide

Sources & evidence

ORD record
ord-d230c0158ba3450b8d969ad661d3ff2d
Source dataset
uspto-grants-1997_10
Patent number
US05681834

Reaction notes

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