Water → HCID 11143440, compound
Reaction equation
[Si:1]([O:8][C@H:9]([CH2:14][C:15](=[O:23])[CH2:16][P:17]([O:21][CH3:22])([O:19][CH3:20])=[O:18])[CH2:10][C:11]([OH:13])=[O:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CI.[C:26](=O)([O-])[O-].[K+].[K+].O>CC(C)=O>[Si:1]([O:8][C@H:9]([CH2:14][C:15](=[O:23])[CH2:16][P:17]([O:19][CH3:20])([O:21][CH3:22])=[O:18])[CH2:10][C:11]([O:13][CH3:26])=[O:12])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
1.05 g of (R)-3-t-butyldimethylsilyloxy-6-dimethoxyphosphinyl-5-oxohexanoic acid prepared above was dissolved in 16 ml of acetone to prepare the solution. To the solution, 2.02 g of methyl iodide and 0.391 g of potassium carbonate were added with stirring, and then the solution was further stirred for 5 hours at room temperature. After 16 ml of water was added to the solution, the solution was extracted with two portions of 20 ml of ethyl acetate. The ethyl acetate portions were combined and dried over anhydrous magnesium sulfate, and then the solvent was removed by distillation in vacuo to give 1.0 g of methyl (R)-3-t-butyldimethylsilyloxy-6-dimethoxyphosphinyl-5-oxohexanoate as an oil (optical purity: 98% ee; yield: 92% based on the amount of (R)-3-t-butyldimethylsilyloxy-6-dimethoxyphosphinyl-5-oxohexanoic acid).
Workup
- customto prepare the solution
- stirringthe solution was further stirred for 5 hours at room temperature
- extractionthe solution was extracted with two portions of 20 ml of ethyl acetate
- dry with materialdried over anhydrous magnesium sulfate
- customthe solvent was removed by distillation in vacuo
Sources & evidence
- ORD record
- ord-6b8be5a2cd5e4e859605b00d27189f66
- Source dataset
- uspto-grants-1998_02
- Patent number
- US05717124
Reaction notes
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