HCID 23530181, compound → 2,6-Naphthalenedicarboxylic acid
Reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([O:10][C@H:11]([CH3:18])[CH2:12][CH:13]([CH2:16][CH3:17])[CH2:14][CH3:15])=[O:9])=[CH:4][CH:3]=1>ClCCl>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:10][C@H:11]([CH3:18])[CH2:12][CH:13]([CH2:16][CH3:17])[CH2:14][CH3:15])=[O:9])=[CH:6][CH:7]=1.[CH:4]1[C:3]2[C:2](=[CH:6][C:5]([C:8]([OH:10])=[O:9])=[CH:4][CH:3]=2)[CH:7]=[CH:6][C:5]=1[C:8]([OH:10])=[O:9]Participants
Reactant 1
Product 2
Reagents, catalysts & solvents 1
Procedure
2.6 Grams (10.3 mmol) of (R)-4-hydroxy-1-(3-ethyl-1-methylpentyloxycarbonyl)benzene obtained in the same manner as in (3) of Example 4, 1.0 g (4.92 mmol) of 2,6-naphthalenedicarboxylic acid and 50 ml of dehydrated dichloromethane were placed in a reactor, 2.3 g (11.1 mmol) of dicyclohexylcarbodiimide and 0.26 g (2.1 mmol) of 4-dimethylaminopyridine were added, and the mixture was stirred at room temperature for 24 hours. To the reaction solution was added 20 ml of water, and the mixture was stirred at room temperature for 1 hour. Then, the reaction mixture was filtered with Celite, and diethyl ether was added to separate a liquid of an organic layer. The organic layer was washed with 2N hydrochloric acid, washed with a 1N sodium hydroxide aqueous solution and then washed with water. The washed organic layer was dried over anhydrous sodium sulfate and filtered, and the solvent was distilled off. The thus-obtained crude product was purified by silica gel chromatography, to give 2.0 g (2.93 mmol, yield 59%) of an end compound.
Sources & evidence
- ORD record
- ord-96846533ed2b46dcaa3bf13c4ba8c850
- Source dataset
- uspto-grants-2004_05
- Patent number
- US06730371B2
Reaction notes
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