Solketal → 4-[(2,2-dimethyl-1,3-dioxolan-4-yl)-methoxycarbonyl]-(S,S)-2,4-dibenzylbutyric acid

HRID 374322Notes

Reaction equation

HRID 374322 reaction equation
[CH2:1]([C@@H:8]1[CH2:14][C@@H:13]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:12](=[O:22])[O:11][C:9]1=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:23][CH2:24][CH:25]1[CH2:29][O:28][C:27]([CH3:31])([CH3:30])[O:26]1>C1(C)C=CC=CC=1>[CH3:30][C:27]1([CH3:31])[O:26][CH:25]([CH2:24][O:23][C:9]([C@H:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:14][C@@H:13]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:12]([OH:11])=[O:22])=[O:10])[CH2:29][O:28]1

Participants

4

Reactant 2

HCID 7528SolketalHCID 14557658(S,S)-2,4-dibenzylglutaric anhydride

Product 1

HCID 149971524-[(2,2-dimethyl-1,3-dioxolan-4-yl)-methoxycarbonyl]-(S,S)-2,4-dibenzylbutyric acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1.0 g of (S,S)-2,4-dibenzylglutaric anhydride and 0.54 g of 4-hydroxymethyl-2,2-dimethyl-1,3-dioxolane in 10 ml of toluene is refluxed overnight. The solution is washed with water, dried (Na2SO4), filtered and concentrated to give 4-[(2,2-dimethyl-1,3-dioxolan-4-yl)-methoxycarbonyl]-(S,S)-2,4-dibenzylbutyric acid as a viscous oil.

Workup

  1. washThe solution is washed with water
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8aa1160ba7564db1b4a3bf00d3c4f906
Source dataset
uspto-grants-1992_11
Patent number
US05166212

Reaction notes

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