Sodium Hydroxide → (S)-(+)-3-(tert-butyl-diphenyl-silanyloxy)-2-methylpropionic acid
Reaction equation
[C:1]([Si:5]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[O:6][CH2:7][C@H:8]([CH3:13])[C:9]([O:11]C)=[O:10])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>O1CCCC1CO>[C:1]([Si:5]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[O:6][CH2:7][C@H:8]([CH3:13])[C:9]([OH:11])=[O:10])([CH3:2])([CH3:3])[CH3:4]Participants
Procedure
This ester (3.15 g, 8.85 mmol) was dissolved in 3:1 tetrahydrofuran-methanol (30 mL) and saponified with aqueous sodium hydroxide (1.0 N, 10.0 mL, 10.0 mmol) overnight at ambient temperature. After concentration, the residue was partitioned between ethyl acetate and water and then acidified (to pH 4–5) with 0.5N aqueous hydrochloric acid. The organic phase was washed with water and brine, dried over anhydrous sodium sulfate and concentrated. Purification was carried out with multiple flash chromatography runs using the Biotage system. Pure fractions from each run were combined and concentrated to yield (S)-3-(tert-butyl-diphenyl-silanyloxy)-2-methylpropionic acid as an oil that solidified to a tacky white solid in the cold. (Yield 2.10 g, 69.2%).
Workup
- concentrationAfter concentration
- customthe residue was partitioned between ethyl acetate and water
- washThe organic phase was washed with water and brine
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated
- customPurification
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-87b5cc174ed44f29966f2600f352099c
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07115740B2
Reaction notes
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