Water → HCID 59326494, compound
Reaction equation
[C:1]([O:5][C:6](=[O:22])[CH2:7]/[C:8](=[CH:14]/[C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)/[CH:9]([CH3:13])[C:10]([OH:12])=O)([CH3:4])([CH3:3])[CH3:2].[C:23](OC(=O)C)(=[O:25])[CH3:24].C([O-])(=O)C.[K+].O>CCCCCCC>[C:1]([O:5][C:6](=[O:22])[CH2:7][C:8]1[C:9]([CH3:13])=[C:10]([O:12][C:23](=[O:25])[CH3:24])[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([F:21])[CH:19]=2)[CH:14]=1)([CH3:2])([CH3:3])[CH3:4]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 85 °C
Procedure
The above prepared 3-[1-(4-fluoro-phenyl)-meth-(Z)-ylidene]-2-methyl-pentanedioic acid 5-tert-butyl ester (38.3 g, 124.2 mmol) was dissolved in acetic anhydride (96.00 mL, 995.3 mmol). To this solution was added potassium acetate (18.66 g, 186.3 mmol), and the reaction mixture was stirred at 85±2° C. for 10 hours, when HPLC analysis showed completed reaction. The reaction mixture was then cooled to room temperature and diluted with 96 mL of heptane. To this solution, 270 mL of water was added over 1 hour, while maintaining the internal temperature at ˜23° C. The mixture was then cooled to 0-5° C., and stirred for 2 hours. The solid formed was filtered, and then washed with water (2×40 mL), heptane (2×40 mL), and then dried under vacuum to furnish 28.5 g of a yellow solid, which was used in the next step without further purification.
Workup
- customreaction
- temperatureThe reaction mixture was then cooled to room temperature
- temperaturewhile maintaining the internal temperature at ˜23° C
- temperatureThe mixture was then cooled to 0-5° C.
- stirringstirred for 2 hours
- customThe solid formed
- filtrationwas filtered
- washwashed with water (2×40 mL), heptane (2×40 mL)
- customdried under vacuum
Sources & evidence
- ORD record
- ord-a4dbe5bbd06a4240a77813723d0bc945
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08642629B2
Reaction notes
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