Water → (S)-2-(tert-butoxycarbonyl)-3-(2,2-dimethylbenzo[d][1,3]dioxol-5-yl)propanoic acid
Reaction equation
C[O:2][C:3](=[O:24])[C@@H:4]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:5][C:6]1[CH:16]=[CH:15][C:9]2[O:10][C:11]([CH3:14])([CH3:13])[O:12][C:8]=2[CH:7]=1.[OH-].[Li+].O>C1COCC1>[C:20]([O:19][C:17]([C@@H:4]([CH2:5][C:6]1[CH:16]=[CH:15][C:9]2[O:10][C:11]([CH3:14])([CH3:13])[O:12][C:8]=2[CH:7]=1)[C:3]([OH:24])=[O:2])=[O:18])([CH3:23])([CH3:21])[CH3:22]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of (S)-methyl2-(tert-butoxycarbonyl)-3-(2,2-dimethylbenzo[d][1,3]dioxol-5-yl)propanoate (5000 mg, 14229 μmol) in 100 mL of THF at 0° C. was added lithium hydroxide (0.2 M, 28458 μl, 14229 μmol) over 10 minutes. After stirring at 0° C. for 1 hour the reaction was poured into a separatory funnel and 100 mL of water was added. The mixture was washed with 150 mL of ether, then acidified to pH 2-3-with 1 N HCl. Ethyl acetate was added, the layers were separated and the aqueous layer was extracted with ethyl acetate (3×100 mL). The combined organics were washed with water and then brine before being dried over sodium sulfate, filtered and concentrated to furnish (S)-2-(tert-butoxycarbonyl)-3-(2,2-dimethylbenzo[d][1,3]dioxol-5-yl)propanoic acid (4005 mg, 83% yield) as a colorless viscous oil.
Workup
- additionwas poured into a separatory funnel
- washThe mixture was washed with 150 mL of ether
- additionEthyl acetate was added
- customthe layers were separated
- extractionthe aqueous layer was extracted with ethyl acetate (3×100 mL)
- washThe combined organics were washed with water
- dry with materialbrine before being dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-0a5ad7e613eb4257bb526fcba10c7896
- Source dataset
- uspto-grants-2010_09
- Patent number
- US07803809B2
Reaction notes
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