Lithium hydroxide, monohydrate → (R)-2-Hydroxy-3-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)propanoic acid
Reaction equation
C([O:4][C@H:5]([CH2:10][C:11]1[CH:19]=[C:18]([CH3:20])[C:17]2[C:13](=[CH:14][N:15]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[N:16]=2)[CH:12]=1)[C:6]([O:8]C)=[O:7])(=O)C.O.[OH-].[Li+]>O1CCCC1.CO.O>[OH:4][C@H:5]([CH2:10][C:11]1[CH:19]=[C:18]([CH3:20])[C:17]2[C:13](=[CH:14][N:15]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:27])([CH3:26])[CH3:28])[N:16]=2)[CH:12]=1)[C:6]([OH:8])=[O:7]Participants
6
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 0 °C
Procedure
To a solution of (R)-methyl 2-acetoxy-3-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)propanoate (700 mg, 1.72 mmol) in tetrahydrofuran (6 mL) and methanol (6 mL) at 0° C. was added a solution of lithium hydroxide monohydrate (289 mg, 6.89 mmol) in water (6 mL). The reaction was stirred at 0° C. for 1 h. The reaction was concentrated, dissolved in 5 mL of water, cooled to 0° C., and treated with 1M hydrochloric acid until mildly acidic. A non-solid ppt formed. The suspension was extracted with ethyl acetate (2×), which were washed with brine, dried over magnesium sulfate, and concentrated to give 620 mg (quant.) which was pure by LC/MS and was used without purification. Mass spec.: 351.13 (MH)+.
Workup
- concentrationThe reaction was concentrated
- dissolutiondissolved in 5 mL of water
- temperaturecooled to 0° C.
- additiontreated with 1M hydrochloric acid until mildly acidic
- customA non-solid ppt formed
- extractionThe suspension was extracted with ethyl acetate (2×), which
- washwere washed with brine
- dry with materialdried over magnesium sulfate
- concentrationconcentrated
- customto give 620 mg (quant.) which
- customwas used without purification
Sources & evidence
- ORD record
- ord-9af57409fd2c41488c07c1472465fa28
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07772244B2
Reaction notes
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