Lithium Hydroxide → 3-Cyclopentyl-2-[4-(1-hydroxy-cyclohexylethynyl)-phenyl]-propionic acid
Reaction equation
C[O:2][C:3](=[O:26])[CH:4]([C:11]1[CH:16]=[CH:15][C:14]([C:17]#[C:18][C:19]2([OH:25])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:13][CH:12]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[OH-].[Li+]>CO.O>[CH:6]1([CH2:5][CH:4]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[C:18][C:19]3([OH:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]3)=[CH:13][CH:12]=2)[C:3]([OH:26])=[O:2])[CH2:7][CH2:8][CH2:9][CH2:10]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 25 °C
Procedure
A solution of 3-cyclopentyl-2-[4-(1-hydroxy-cyclohexylethynyl)-phenyl]-propionic acid methyl ester (753 mg, 2.0 mmol) in methanol (10 mL) and water (10 mL) was treated with lithium hydroxide (1.02 g, 24.3 mmol). The reaction mixture was stirred at 25° C. for 18 h. At this time, the reaction was concentrated in vacuo. The residue was diluted with water (40 mL). This solution was acidified to pH=2 with concentrated hydrochloric acid and then extracted with ethyl acetate (2×40 mL). The combined organic extracts were then washed with a half-saturated sodium chloride solution (1×40 mL), dried over sodium sulfate, filtered, and concentrated in vacuo to afford 3-cyclopentyl-2-[4-(1-hydroxy-cyclohexylethynyl)-phenyl]-propionic acid (727 mg, quant.) as an amber foam: EI-HRMS m/e calcd for C22H28O3 (M+) 340.2038, found 340.2037.
Workup
- concentrationAt this time, the reaction was concentrated in vacuo
- additionThe residue was diluted with water (40 mL)
- extractionextracted with ethyl acetate (2×40 mL)
- washThe combined organic extracts were then washed with a half-saturated sodium chloride solution (1×40 mL)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-5c236adef0454d35ac442af5259bde86
- Source dataset
- uspto-grants-2002_05
- Patent number
- US06388071B2
Reaction notes
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