Hydrochloric Acid → HCID 22093949, compound
Reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH:4]([OH:17])[CH2:5][CH2:6][NH:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)=[O:9].[H-].[Na+].Br[CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24].Cl>O1CCCC1>[CH3:1][O:2][C:3](=[O:18])[CH:4]([O:17][CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:5][CH2:6][NH:7][C:8]([C:10]1[CH:11]=[CH:12][C:13]([Cl:16])=[CH:14][CH:15]=1)=[O:9]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of 4-(N-(4-chlorophenylcarbonyl)amino)-2-hydroxybutyric acid methyl ester (3 g) in tetrahydrofuran (15 ml) was dropped to a mixture of 60% sodium hydride (2.38 g) in tetrahydrofuran (10 ml) at −78° C. The mixture was stirred at 0° C. for 30 minutes. t-Butyl bromoacetate (0.975 g) was dropped to the mixture at −78° C. The mixture was stirred at 0° C. for 1.5 hours. To the reaction mixture, 1N hydrochloric acid was added and the mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium hydrogen carbonate and a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (n-Hexane:Ethyl acetate=1:1) to give the title compound (3.194 g) having the following physical data.
Workup
- stirringThe mixture was stirred at 0° C. for 1.5 hours
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed with a saturated aqueous solution of sodium hydrogen carbonate
- dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate
- concentrationconcentrated
- customThe residue was purified by column chromatography on silica gel (n-Hexane:Ethyl acetate=1:1)
Sources & evidence
- ORD record
- ord-c977c862da95489f8b2f25084ee884b2
- Source dataset
- uspto-grants-2002_07
- Patent number
- US06420427B1
Reaction notes
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