Hydrochloric Acid → HCID 66661273, compound
Reaction equation
[F:1][C:2]([F:21])([CH3:20])[CH2:3][C@H:4]1[C:8](=[O:9])[O:7]C[N:5]1[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11].[OH-].[Na+].Cl>CC(C)=O>[CH2:13]([O:12][C:10]([NH:5][C@@H:4]([CH2:3][C:2]([F:1])([F:21])[CH3:20])[C:8]([OH:9])=[O:7])=[O:11])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
The compound from example 14 (4.9 g, 16.37 mmol) was dissolved in 30 ml of acetone and cooled to 0° C., and then 1 N sodium hydroxide solution (32.74 ml, 32.74 mmol, 2 eq.) was added. For about 2.5 h, the reaction mixture was stirred at room temperature; reaction monitoring by LC-MS indicated complete conversion. This was followed by addition of 20 ml of 1 N HCl, distilling-off of acetone under reduced pressure and adjustment of the solution to pH 3 to 4. The mixture was extracted twice by shaking with ethyl acetate. The organic phase was washed with saturated NaCl solution, dried over sodium sulfate and concentrated by evaporation to dryness under reduced pressure. The crude product was chromatographed using silica gel with a DCM/methanol gradient (0-6% methanol).
Workup
- customreaction monitoring by LC-MS
- extractionThe mixture was extracted twice
- stirringby shaking with ethyl acetate
- washThe organic phase was washed with saturated NaCl solution
- dry with materialdried over sodium sulfate
- concentrationconcentrated by evaporation to dryness under reduced pressure
- customThe crude product was chromatographed
Sources & evidence
- ORD record
- ord-a7dfad71ca7b451db9d8ee24e0304f26
- Source dataset
- uspto-grants-2011_10
- Patent number
- US08039480B2
Reaction notes
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