Hydrochloric Acid → (3R)-3-(3-Isoxazolyl)-3-(3-((phenylmethyl)oxy)phenyl)propanoic acid
Reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C@@H:6]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH:24]=2)[CH2:7][C:8](N2[C@H](CC3C=CC=CC=3)COC2=O)=[O:9])=[N:2]1.[OH:37]O.[Li+].[OH-].Cl>C1COCC1.O>[O:1]1[CH:5]=[CH:4][C:3]([C@@H:6]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH:24]=2)[CH2:7][C:8]([OH:9])=[O:37])=[N:2]1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
A solution of (R)-4-benzyl-3-((R)-3-(3-(benzyloxy)phenyl)-3-(isoxazol-3-yl)propanoyl)oxazolidin-2-one (94.1C) (0.558 g, 1.16 mmol) in THF (12 mL) was cooled to 0° C. H2O2 (30% w/w, 0.50 mL) was added, and was followed by addition of LiOH, monohydrate (0.0643 mL, 2.31 mmol) in water (4 mL). The resulting mixture was stirred at 0° C. for 2 hours. The organic solvent was blown away by nitrogen, and the aqueous mixture was acidified with 1N HCl to pH 3-5. The mixture was extracted with EtOAc (100 mL). The organic phase was washed with brine, dried over anhydrous Na2SO4. After removing solvent, crude product (94.1D) (491 mg) was obtained.
Workup
- extractionThe mixture was extracted with EtOAc (100 mL)
- washThe organic phase was washed with brine
- dry with materialdried over anhydrous Na2SO4
- customAfter removing solvent
Sources & evidence
- ORD record
- ord-0e6d1673694d4a1393e44a481bc19fb3
- Source dataset
- uspto-grants-2011_10
- Patent number
- US08030354B2
Reaction notes
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