Hydrochloric Acid → [Rac]-3-[4-(2-tert-butyl-5-methyl-oxazol-4-ylmethoxy)-2-methyl-phenyl]-2-ethoxy-propionic acid
Reaction equation
C([O:3][C:4](=[O:29])[CH:5]([O:26][CH2:27][CH3:28])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[N:16]=[C:17]([C:21]([CH3:24])([CH3:23])[CH3:22])[O:18][C:19]=2[CH3:20])=[CH:9][C:8]=1[CH3:25])C.[Li+].[OH-].Cl>C1COCC1.CO>[C:21]([C:17]1[O:18][C:19]([CH3:20])=[C:15]([CH2:14][O:13][C:10]2[CH:11]=[CH:12][C:7]([CH2:6][CH:5]([O:26][CH2:27][CH3:28])[C:4]([OH:29])=[O:3])=[C:8]([CH3:25])[CH:9]=2)[N:16]=1)([CH3:23])([CH3:24])[CH3:22]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of [rac]-3-[4-(2-tert-butyl-5-methyl-oxazol-4-ylmethoxy)-2-methyl-phenyl]-2-ethoxy-propionic acid ethyl ester (50 mg, 0.124 mmol) in THF/methanol 2/1 (0.75 ml) was added a 1 N aqueous LiOH solution (0.75 ml, 0.72 mmol). The reaction mixture was stirred for 2 h at ambient temperature, neutralized with 1 N aqueous HCl solution under ice cooling and concentrated under reduced pressure. The residue was dissolved in 1 N HCl/ice water 1/1 and ethyl acetate, the layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with ice water/brine 1/1, dried over sodium sulfate and the solvent was evaporated in vacuo to give the title compound (44 mg, 0.117 mmol, 95%) as colorless crystals.
Workup
- concentrationconcentrated under reduced pressure
- dissolutionThe residue was dissolved in 1 N HCl/ice water 1/1
- customethyl acetate, the layers were separated
- extractionthe aqueous layer was extracted with ethyl acetate
- washThe combined organic layers were washed with ice water/brine 1/1
- dry with materialdried over sodium sulfate
- customthe solvent was evaporated in vacuo
Sources & evidence
- ORD record
- ord-016d44fa08f146e8822ec5f92ebba9fe
- Source dataset
- uspto-grants-2006_09
- Patent number
- US07109225B2
Reaction notes
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