2,2-Dimethoxypropane → (2R)-2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]-3-phenylpropanoic acid

HRID 888213Notes

Reaction equation

HRID 888213 reaction equation
[CH2:1]([C@H:8]([C@H:12]([OH:16])[C:13]([OH:15])=[O:14])[C:9]([OH:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO[C:19](OC)([CH3:21])[CH3:20]>CC(C)=O.[Cu](Cl)Cl>[CH3:20][C:19]1([CH3:21])[O:16][C@@H:12]([C@@H:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:9]([OH:11])=[O:10])[C:13](=[O:15])[O:14]1

Participants

5

Reactant 2

HCID 64952,2-DimethoxypropaneHCID 54300227(2R,3S)-2-benzyl-3-hydroxysuccinic acid

Product 1

HCID 58488000(2R)-2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]-3-phenylpropanoic acidYield 72.9%

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 180AcetoneSolvent

Procedure

To a solution of (2R,3S)-2-benzyl-3-hydroxysuccinic acid (1.70 g; 7.58 mmol; 1.0 eq.) in acetone (50.0 mL) was added 2,2-dimethoxypropane (1.86 g; 15.2 mmol; 2.0 eq.) and copper(II) chloride (102 mg; 0.76 mmol; 0.1 eq.). The resulting reaction mixture was stirred for 2 h at RT. The reaction mixture was evaporated and the residue taken up in CHCl3. Activated charcoal is added and the resulting mixture stirred for one hour. Filtration on a pad of celite gave the title product as a greenish oil (1.46 g) used in the next step without further purification.

Workup

  1. customThe resulting reaction mixture
  2. customThe reaction mixture was evaporated
  3. additionActivated charcoal is added
  4. stirringthe resulting mixture stirred for one hour
  5. filtrationFiltration on a pad of celite

Sources & evidence

ORD record
ord-a3d38328451c48bf9b632a80efed669f
Source dataset
uspto-grants-2012_08
Patent number
US08247437B2

Reaction notes

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