p-Toluenesulfonic acid → HCID 22256526, compound

HRID 1008281Notes

Reaction equation

HRID 1008281 reaction equation
[CH2:1]([C@@H:5]([C:11]([OH:13])=[O:12])[C@H:6]([OH:10])[C:7]([OH:9])=[O:8])[CH2:2][CH2:3][CH3:4].[C:14]1(C)[CH:19]=CC(S(O)(=O)=O)=C[CH:15]=1>COC(OC)(C)C.ClCCl>[CH3:15][C:14]1([CH3:19])[O:8][C:7](=[O:9])[CH:6]([CH:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:11]([OH:13])=[O:12])[O:10]1

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 60111363(2S,3R)-3-(n-butyl)-2-hydroxysuccinic acid

Product 1

HCID 22256526HCID 22256526, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 64952,2-DimethoxypropaneSolvent

Procedure

To a solution of (2S, 3R)-3-(n-butyl)-2-hydroxysuccinic acid F-4 (300 mg, 1.58 mmol) in 2,2-dimethoxypropane (10 mL) was added p-toluenesulfonic acid (20 mg) and the reaction was stirred at room temperature for 16 h. The solution was diluted with dichloromethane and washed with brine, dried (Na2SO4) and then purified by silica gel chromatography to afford 1.2 mmol 2-(2,2-dimethyl-4-oxo-1,3-dioxolan-5-yl)hexanoic acid F-5 (78%).

Workup

  1. washwashed with brine
  2. dry with materialdried (Na2SO4)
  3. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-e9e5b84286444fde9e5e254400c0bfa4
Source dataset
uspto-grants-2004_09
Patent number
US06797820B2

Reaction notes

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