Hydrogen Peroxide → HCID 15870214, compound
Reaction equation
[BH4-].[Na+].CSC.[CH3:6][O:7][C:8](=[O:22])[CH2:9][C@@H:10]([S:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:11](O)=[O:12].[OH-].[Na+].OO.[Cl-].[Na+]>O1CCCC1>[CH3:6][O:7][C:8](=[O:22])[CH2:9][C@@H:10]([S:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH2:11][OH:12]Participants
Procedure
To a suspension of sodium borohydride (1.78 g) in tetrahydrofuran (70 ml)is added dimethylsulfide (2.8 ml) at room temperature, and thereto is added dropwise a solution of boron trifluoride·ether complex (6.3 ml) in tetrahydrofuran (10 ml) at room temperature, and the mixture is stirred for 30 minutes. To the mixture is added (3R)-3-benzylthio-3-carboxypropionic acid methyl ester (10 g) at room temperature, and the mixture is stirred for 1.5 hour. After the reaction is completed, to the reaction solution are added successively 2N aqueous sodium hydroxide solution (16 ml), 30% aqueous hydrogen peroxide solution (11 ml), and then further added a saturated aqueous sodium chloride solution. The mixture is extracted with chloroform, and the extract is dried, concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (solvent; n-hexane:ethyl acetate=2:1) to give (3R)-3-benzylthio-4-hydroxybutyric acid methyl ester (7.75 g) as an oily product.
Workup
- stirringthe mixture is stirred for 1.5 hour
- extractionThe mixture is extracted with chloroform
- customthe extract is dried
- concentrationconcentrated under reduced pressure
- customthe residue is purified by silica gel column chromatography (solvent; n-hexane:ethyl acetate=2:1)
Sources & evidence
- ORD record
- ord-a8e4e6fcd8f14bcc9cedcf551546834c
- Source dataset
- uspto-grants-1997_05
- Patent number
- US05629419
Reaction notes
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