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CAS No.: | 195202-08-5 | ||
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Name: | (S)-2-(3,4,5-TRIMETHOXYPHENYL)BUTYRIC ACID | ||
Article Data: | 5 | ||
Molecular Structure: | |||
Formula: | C13H18 O5 | ||
Molecular Weight: | 254.283 | ||
Synonyms: | Benzeneaceticacid, a-ethyl-3,4,5-trimethoxy-, (S)-(9CI); (S)-2-(3,4,5-Trimethoxyphenyl)butyric acid | ||
Density: | 1.142g/cm3 | ||
Boiling Point: | 378.9°Cat760mmHg | ||
Flash Point: | 138.7°C | ||
Hazard Symbols: | |||
Risk Codes: | Xi:; "> Xi:; |
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Safety: |
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PSA: | 64.99000 | ||
LogP: | 2.29060 |
ethyl iodide
(2S)-2-(3,4,5-trimethoxyphenyl)butanoic acid
Conditions | Yield |
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Stage #1: 3,4,5-trimethoxyphenyl acetic acid; N1,N3-bis((R)-1-phenyl-2-(piperidin-1-yl)ethyl)propane-1,3-diamine With n-butyllithium In tetrahydrofuran; hexane at -78 - 0℃; for 0.333333h; Stage #2: ethyl iodide In tetrahydrofuran; hexane at -78℃; for 2.5h; | 81% |
2-ethyl-(3,4,5-trimethoxyphenyl)acetic acid
(2S)-2-(3,4,5-trimethoxyphenyl)butanoic acid
Conditions | Yield |
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With Cinchonidin In acetonitrile at 20℃; | 48.5% |
Stage #1: 2-ethyl-(3,4,5-trimethoxyphenyl)acetic acid With cinchonidine In acetonitrile Separation of racemate; Stage #2: With hydrogenchloride In dichloromethane; water pH=2; Separation of racemate; | 21% |
3,4,5-trimethoxyphenyl acetic acid
(2S)-2-(3,4,5-trimethoxyphenyl)butanoic acid
Conditions | Yield |
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Multi-step reaction with 2 steps 1.1: potassium hexamethylsilazane / tetrahydrofuran / 1.5 h / -25 - -15 °C / Inert atmosphere 1.2: -25 - 20 °C 2.1: cinchonidine / acetonitrile / Separation of racemate 2.2: pH 2 / Separation of racemate View Scheme | |
Multi-step reaction with 2 steps 1: sodium hexamethyldisilazane / tetrahydrofuran / -25 - 20 °C 2: Cinchonidin / acetonitrile / 20 °C View Scheme |
(2S)-2-(3,4,5-trimethoxyphenyl)butanoic acid
Conditions | Yield |
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Stage #1: X With sulfuric acid In 1,4-dioxane; water for 2h; Reflux; Stage #2: With sodium hydroxide In 1,4-dioxane; water pH=12; Stage #3: In 1,4-dioxane; water pH=3; |
(+)-<1'S,2'S>-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-N-methyl-2-(3,4,5-trimethoxyphenyl)acetamide
(2S)-2-(3,4,5-trimethoxyphenyl)butanoic acid
Conditions | Yield |
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Multi-step reaction with 2 steps 1.1: lithium hexamethyldisilazane; lithium chloride / tetrahydrofuran / 1 h / -5 °C 1.2: 3 h / -5 °C 2.1: sulfuric acid / 1,4-dioxane; water / 2 h / Reflux 2.2: pH 12 2.3: pH 3 View Scheme |
(2S)-2-(3,4,5-trimethoxyphenyl)butanoic acid
Conditions | Yield |
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With thionyl chloride In dichloromethane for 2h; Reflux; | 100% |
(2S)-2-(3,4,5-trimethoxyphenyl)butanoic acid
(S)-methyl pipecolinate hydrochloride
(S)-1-((S)-2-(3,4,5-trimethoxyphenyl)butanoyl)piperidine-2-carboxylic acid
Conditions | Yield |
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Stage #1: (2S)-2-(3,4,5-trimethoxyphenyl)butanoic acid; (S)-methyl pipecolinate hydrochloride With 2-chloro-1-methyl-pyridinium iodide; triethylamine In dichloromethane at 20℃; for 2h; Stage #2: With lithium hydroxide In dichloromethane; water at 20℃; | 84% |
Stage #1: (2S)-2-(3,4,5-trimethoxyphenyl)butanoic acid; (S)-methyl pipecolinate hydrochloride With 2-chloro-1-methyl-pyridinium iodide; triethylamine In dichloromethane at 22℃; for 2h; Stage #2: With lithium hydroxide monohydrate; water In methanol Stage #3: With hydrogenchloride In water pH=4; | 73% |
Stage #1: (2S)-2-(3,4,5-trimethoxyphenyl)butanoic acid; (S)-methyl pipecolinate hydrochloride With 2-chloro-1-methyl-pyridinium iodide; triethylamine In dichloromethane at 12 - 25℃; Stage #2: With lithium hydroxide monohydrate In methanol; water at 22℃; for 12h; | 66% |
Multi-step reaction with 2 steps 1: 2-chloro-1-methyl-pyridinium iodide; triethylamine / dichloromethane / 12 - 25 °C 2: lithium hydroxide monohydrate / water; methanol / 12 h / 22 °C View Scheme |
(2S)-2-(3,4,5-trimethoxyphenyl)butanoic acid
(1R)-3-(3,4-dimethoxyphenyl)-1-[3-(t-butoxycarbonylmethoxy)phenyl]-1-propyl (2S)-2-piperidine carboxylate
(R)-1-(3-(2-(tert-butoxy)-2-oxoethoxy)phenyl)-3-(3,4-dimethoxyphenyl)propyl (S)-1-((S)-2-(3,4,5-trimethoxyphenyl)butanoyl)piperidine-2-carboxylate
Conditions | Yield |
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With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 24h; Inert atmosphere; | 58% |
With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride | 55% |
(2S)-2-(3,4,5-trimethoxyphenyl)butanoic acid
(R)-3-(3,4-dimethoxyphenyl)-1-(3-(2-morpholinoethoxy)phenyl)propyl (S)-1-((S)-2-(3,4,5-trimethoxyphenyl)butanoyl)piperidine-2-carboxylate
Conditions | Yield |
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Multi-step reaction with 3 steps 1: thionyl chloride / dichloromethane / 2 h / Reflux 2: sodium hydrogencarbonate / 1,4-dioxane / 22 h / Reflux 3: dmap; diisopropyl-carbodiimide / dichloromethane / 3 h / 0 - 20 °C View Scheme |
(2S)-2-(3,4,5-trimethoxyphenyl)butanoic acid
(S)-1-((S)-2-(3,4,5-trimethoxyphenyl)butanoyl)piperidine-2-carboxylic acid
Conditions | Yield |
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Multi-step reaction with 2 steps 1: thionyl chloride / dichloromethane / 2 h / Reflux 2: sodium hydrogencarbonate / 1,4-dioxane / 22 h / Reflux View Scheme |