p-Toluenesulfonic acid → HCID 22256526, compound

HRID 1611246Notes

Reaction equation

HRID 1611246 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].[CH3:14][C:15]1C=CC(S(O)(=O)=O)=C[CH:20]=1>COC(OC)(C)C.C(Cl)Cl>[CH3:14][C:15]1([CH3:20])[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 B-4 (300 mg, 1.58 mmol) in 2,2-dimethoxypropane (10 mL) is added p-TSA (20 mg) and the reaction is stirred at rt for 16 hours. The solution is diluted with DCM 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 B-5.

Workup

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

Sources & evidence

ORD record
ord-d271d9e6220a4fce96321d7f2a58011d
Source dataset
uspto-grants-2006_01
Patent number
US06987104B2

Reaction notes

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