Hydrochloric Acid → HCID 57144426, compound
Reaction equation
C[O:2][C:3]([C@@H:5]1[O:9][C:8](=[O:10])[N:7]([C:11](=[O:29])[NH:12][CH2:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][CH:19]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[CH2:18][CH2:17]2)[C@H:6]1[C:30]1[CH:35]=[CH:34][C:33]([F:36])=[C:32]([F:37])[CH:31]=1)=[O:4].[OH-].[Li+].Cl>O1CCCC1>[F:37][C:32]1[CH:31]=[C:30]([C@H:6]2[C@H:5]([C:3]([OH:4])=[O:2])[O:9][C:8](=[O:10])[N:7]2[C:11](=[O:29])[NH:12][CH2:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][CH:19]([C:22]3[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=3)[CH2:18][CH2:17]2)[CH:35]=[CH:34][C:33]=1[F:36]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of the hydrochloride salt of (4S, 5R)-4-(3,4-difluorophenyl)-3-{3-[4-(4-fluorophenyl)piperidin-1-yl]propylcarbamoyl}-2-oxo-oxazolidine-5-carboxylic acid methyl ester (300 mg, 0.54 mmol) in tetrahydrofuran (5 mL) was cooled to 0° C. and treated with 0.5M aqueous lithium hydroxide solution (2.2 mL, 1.1 mmol). The reaction mixture was stirred at 0° C. 20 minutes when 1N aqueous HCl was added dropwise until the pH of the reaction mixture reached 6. The volatile organics were removed under reduced pressure and the resulting aqueous solution extracted with dichloromethane (3×50 mL). The combined organics were dried over sodium sulfate, filtered and the volatiles removed to provide (4S, 5R)-4-(3,4-difluorophenyl)-3-{3-[4-(4-fluorophenyl)piperidin-1-yl]propylcarbamoyl}-2-oxo-oxazolidine-5-carboxylic acid as a foam.
Workup
- customThe volatile organics were removed under reduced pressure
- extractionthe resulting aqueous solution extracted with dichloromethane (3×50 mL)
- dry with materialThe combined organics were dried over sodium sulfate
- filtrationfiltered
- customthe volatiles removed
Sources & evidence
- ORD record
- ord-c48f0bbcea98410696eb5ba3b26a009e
- Source dataset
- uspto-grants-2001_11
- Patent number
- US06319932B1
Reaction notes
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