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

HRID 888216Notes

Reaction equation

HRID 888216 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 58487960(2S)-2-[(4R)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]-3-phenylpropanoic acidYield 74%

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 180AcetoneSolvent

Procedure

To a solution of (2R,3S)-2-benzyl-3-hydroxysuccinic acid (2.08 g; 9.28 mmol; 1.00 eq.) in acetone (50.0 mL) was added 2,2-dimethoxypropane (2.3 mL; 18.55 mmol; 2.0 eq.) and copper(II) chloride (124.73 mg; 0.93 mmol; 0.10 eq.). The resulting reaction mixture was stirred for 4 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 (single diastereoisomer) as a greenish oil (1.81 g, 74%) 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-54df70591d16431db6664017e39c134c
Source dataset
uspto-grants-2012_08
Patent number
US08247437B2

Reaction notes

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