Carbon Dioxide → HCID 67282685, compound
Reaction equation
Br[C:2]1[C:20]([CH3:21])=[CH:19][C:5]([O:6][CH2:7][C@@H:8]2[CH2:13][N:12]([CH3:14])[C:11]3[CH:15]=[CH:16][CH:17]=[CH:18][C:10]=3[O:9]2)=[CH:4][C:3]=1[CH3:22].C([Li])CCC.[C:28](=[O:30])=[O:29]>O1CCCC1>[CH3:22][C:3]1[CH:4]=[C:5]([O:6][CH2:7][C@@H:8]2[CH2:13][N:12]([CH3:14])[C:11]3[CH:15]=[CH:16][CH:17]=[CH:18][C:10]=3[O:9]2)[CH:19]=[C:20]([CH3:21])[C:2]=1[C:28]([OH:30])=[O:29]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Under an argon atmosphere, the compound (219 g) prepared in Example 8 was dissolved in anhydrous tetrahydrofuran (1.7 L) and stirred at −78° C. n-butyl lithium (1.58 M n-hexane solution, 421 mL) was added to the solution and was stirred for 1 hour. After carbon dioxide was blown into the solution, the solution was stirred for 2 hours while heating up to 0° C. After the residue obtained by removing the solvent was diluted with 1N sodium hydroxide aqueous solution, the solution was washed by tert-butylmethylether. A 5N hydrochloric acid was added to the aqueous phase while stirring to obtain a crystal. The title compound (183 g) having the following physical data was obtained by filtrating and drying the crystal.
Workup
- additionwas added to the solution
- stirringthe solution was stirred for 2 hours
- customAfter the residue obtained
- customby removing the solvent
- additionwas diluted with 1N sodium hydroxide aqueous solution
- washthe solution was washed by tert-butylmethylether
- additionA 5N hydrochloric acid was added to the aqueous phase
- stirringwhile stirring
- customto obtain a crystal
Sources & evidence
- ORD record
- ord-ed7e381c51df46afac0fd49ec91e38b9
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08809524B2
Reaction notes
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