Gamma-Aminobutyric Acid → HCID 123537105, compound
Reaction equation
[CH:1]([SiH:4]([CH:14]([CH3:16])[CH3:15])[C:5]1[CH:13]=[CH:12][C:8]([C:9](Cl)=[O:10])=[CH:7][CH:6]=1)([CH3:3])[CH3:2].[OH-].[Na+].[NH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24].Cl>>[CH:1]([SiH:4]([CH:14]([CH3:16])[CH3:15])[C:5]1[CH:13]=[CH:12][C:8]([C:9]([NH:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])=[O:10])=[CH:7][CH:6]=1)([CH3:3])[CH3:2]Participants
Procedure
4-diisopropylsilanylbenzoyl chloride (2) (1.7 g, 6.7 mmol) was added into 1N sodium hydroxide aqueous solution (9 mL) dissolving 4-aminobutanoic acid (910 mg. 8.94 mmol) and stirred for 8 hours. After the addition of 12N hydrochloric acid to the aqueous solution to reach pH 2, the solution was extracted with 400 mL of CH2Cl2 and an organic layer was then collected. The resulting organic layer was dehydrated with anhydrous sodium sulfate and filtered so that the resulting solvent was distilled out under a reduced pressure. A desired compound was then purified by silica gel column chromatography. After eluted with chloroform having 0-3% methanol gradient, the solvent was distilled out to give the desired compound as white solid (1.4 g, 65%). Its NMR data are as follows:
Workup
- extractionthe solution was extracted with 400 mL of CH2Cl2
- customan organic layer was then collected
- filtrationfiltered so that the resulting solvent
- distillationwas distilled out under a reduced pressure
- customA desired compound was then purified by silica gel column chromatography
- washAfter eluted with chloroform having 0-3% methanol gradient
- distillationthe solvent was distilled out
Sources & evidence
- ORD record
- ord-0a3055462a31423ead7a1f648bd7c078
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07786296B2
Reaction notes
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