2,2-Dimethoxypropane → (2R)-2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]-5-[4-(trifluoro methoxy)phenyl]pentanoic acid
Reaction equation
[OH:1][C@@H:2]([C@@H:6]([CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=1)[C:7]([OH:9])=[O:8])[C:3]([OH:5])=[O:4].CO[C:26](OC)([CH3:28])[CH3:27]>CC(C)=O.[Cu](Cl)Cl>[CH3:27][C:26]1([CH3:28])[O:1][C@@H:2]([C@@H:6]([CH2:10][CH2:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([O:19][C:20]([F:21])([F:22])[F:23])=[CH:17][CH:18]=2)[C:7]([OH:9])=[O:8])[C:3](=[O:5])[O:4]1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of (2S,3R)-2-hydroxy-3-{3-[4-(trifluoromethoxy)phenyl]propyl}butanedioic acid (5.58 g; 16.6 mmol; 1.0 eq.) in acetone (61 mL) was added 2,2-dimethoxypropane (3.5 mL; 28.2 mmol; 1.70 eq.) and copper(II) chloride (220 mg; 1.66 mmol; 0.1 eq.). The resulting reaction mixture was stirred 14 h at RT. The reaction mixture was evaporated and the residue taken up in Et2O and filtered on a pad of cellite. The liquids were evaporated again and the residue was treated with activated charcoal in Et2O and filtered on a pad of cellite to give the title product as a greenish oil used in the next step without further purification. (5.85 g; 93.7%). M+(ESI): 377.0; M−(ESI): 375.1.
Workup
- customThe resulting reaction mixture
- customThe reaction mixture was evaporated
- filtrationfiltered on a pad of cellite
- customThe liquids were evaporated again
- additionthe residue was treated with activated charcoal in Et2O
- filtrationfiltered on a pad of cellite
Sources & evidence
- ORD record
- ord-f47ba1b7fdf64b719220ad7a4c670ae0
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08247437B2
Reaction notes
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