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195202-08-5

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195202-08-5 Usage

Uses

(S)-2-(3,4,5-Trimethoxyphenyl)butyric Acid, is a building block used in various chemical synthesis.

Check Digit Verification of cas no

The CAS Registry Mumber 195202-08-5 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,9,5,2,0 and 2 respectively; the second part has 2 digits, 0 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 195202-08:
(8*1)+(7*9)+(6*5)+(5*2)+(4*0)+(3*2)+(2*0)+(1*8)=125
125 % 10 = 5
So 195202-08-5 is a valid CAS Registry Number.
InChI:InChI=1/C13H18O5/c1-5-9(13(14)15)8-6-10(16-2)12(18-4)11(7-8)17-3/h6-7,9H,5H2,1-4H3,(H,14,15)/t9-/m0/s1

195202-08-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name (S)-2-(3,4,5-TRIMETHOXYPHENYL)BUTYRIC ACID

1.2 Other means of identification

Product number -
Other names S-(3,4,5-Trimethoxyphenyl)butyric acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:195202-08-5 SDS

195202-08-5Synthetic route

N1,N3-bis((R)-1-phenyl-2-(piperidin-1-yl)ethyl)propane-1,3-diamine

N1,N3-bis((R)-1-phenyl-2-(piperidin-1-yl)ethyl)propane-1,3-diamine

ethyl iodide
75-03-6

ethyl iodide

(2S)-2-(3,4,5-trimethoxyphenyl)butanoic acid
195202-08-5

(2S)-2-(3,4,5-trimethoxyphenyl)butanoic acid

Conditions
ConditionsYield
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
195202-06-3

2-ethyl-(3,4,5-trimethoxyphenyl)acetic acid

(2S)-2-(3,4,5-trimethoxyphenyl)butanoic acid
195202-08-5

(2S)-2-(3,4,5-trimethoxyphenyl)butanoic acid

Conditions
ConditionsYield
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
951-82-6

3,4,5-trimethoxyphenyl acetic acid

(2S)-2-(3,4,5-trimethoxyphenyl)butanoic acid
195202-08-5

(2S)-2-(3,4,5-trimethoxyphenyl)butanoic acid

Conditions
ConditionsYield
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
195202-08-5

(2S)-2-(3,4,5-trimethoxyphenyl)butanoic acid

Conditions
ConditionsYield
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
247118-51-0

(+)-<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
195202-08-5

(2S)-2-(3,4,5-trimethoxyphenyl)butanoic acid

Conditions
ConditionsYield
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
195202-08-5

(2S)-2-(3,4,5-trimethoxyphenyl)butanoic acid

(S)-2-(3,4,5-trimethoxyphenyl)butanoyl chloride

(S)-2-(3,4,5-trimethoxyphenyl)butanoyl chloride

Conditions
ConditionsYield
With thionyl chloride In dichloromethane for 2h; Reflux;100%
(2S)-2-(3,4,5-trimethoxyphenyl)butanoic acid
195202-08-5

(2S)-2-(3,4,5-trimethoxyphenyl)butanoic acid

(S)-methyl pipecolinate hydrochloride
18650-39-0

(S)-methyl pipecolinate hydrochloride

(S)-1-((S)-2-(3,4,5-trimethoxyphenyl)butanoyl)piperidine-2-carboxylic acid
195202-09-6

(S)-1-((S)-2-(3,4,5-trimethoxyphenyl)butanoyl)piperidine-2-carboxylic acid

Conditions
ConditionsYield
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
195202-08-5

(2S)-2-(3,4,5-trimethoxyphenyl)butanoic acid

(1R)-3-(3,4-dimethoxyphenyl)-1-[3-(t-butoxycarbonylmethoxy)phenyl]-1-propyl (2S)-2-piperidine carboxylate
195202-03-0

(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
195202-26-7

(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
ConditionsYield
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 hydrochloride55%
(2S)-2-(3,4,5-trimethoxyphenyl)butanoic acid
195202-08-5

(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
914805-33-7

(R)-3-(3,4-dimethoxyphenyl)-1-(3-(2-morpholinoethoxy)phenyl)propyl (S)-1-((S)-2-(3,4,5-trimethoxyphenyl)butanoyl)piperidine-2-carboxylate

Conditions
ConditionsYield
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
195202-08-5

(2S)-2-(3,4,5-trimethoxyphenyl)butanoic acid

(S)-1-((S)-2-(3,4,5-trimethoxyphenyl)butanoyl)piperidine-2-carboxylic acid
195202-09-6

(S)-1-((S)-2-(3,4,5-trimethoxyphenyl)butanoyl)piperidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: thionyl chloride / dichloromethane / 2 h / Reflux
2: sodium hydrogencarbonate / 1,4-dioxane / 22 h / Reflux
View Scheme
(2S)-2-(3,4,5-trimethoxyphenyl)butanoic acid
195202-08-5

(2S)-2-(3,4,5-trimethoxyphenyl)butanoic acid

(R)-1-(3-((19-(4-((2,4-diaminopyrimidin-5-yl)methyl)-2,6-dimethoxyphenoxy)-2,18-dioxo-7,10,13-trioxa-3,17-diazanonadecyl)oxy)phenyl)-3-(3,4-dimethoxyphenyl)propyl (S)-1-((S)-2-(3,4,5-trimethoxyphenyl)butanoyl)piperidine-2-carboxylate

(R)-1-(3-((19-(4-((2,4-diaminopyrimidin-5-yl)methyl)-2,6-dimethoxyphenoxy)-2,18-dioxo-7,10,13-trioxa-3,17-diazanonadecyl)oxy)phenyl)-3-(3,4-dimethoxyphenyl)propyl (S)-1-((S)-2-(3,4,5-trimethoxyphenyl)butanoyl)piperidine-2-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane / 24 h / 20 °C / Inert atmosphere
2: trifluoroacetic acid / dichloromethane / 20 °C
3: benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 8 h / 20 °C / Inert atmosphere
View Scheme
(2S)-2-(3,4,5-trimethoxyphenyl)butanoic acid
195202-08-5

(2S)-2-(3,4,5-trimethoxyphenyl)butanoic acid

2-(3-((R)-3-(3,4-dimethoxyphenyl)-1-(((S)-1-((S)-2-(3,4,5-trimethoxyphenyl)butanoyl)piperidine-2-carbonyl)oxy)propyl)phenoxy)acetic acid

2-(3-((R)-3-(3,4-dimethoxyphenyl)-1-(((S)-1-((S)-2-(3,4,5-trimethoxyphenyl)butanoyl)piperidine-2-carbonyl)oxy)propyl)phenoxy)acetic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane / 24 h / 20 °C / Inert atmosphere
2: trifluoroacetic acid / dichloromethane / 20 °C
View Scheme
(2S)-2-(3,4,5-trimethoxyphenyl)butanoic acid
195202-08-5

(2S)-2-(3,4,5-trimethoxyphenyl)butanoic acid

(S)-methyl pipecolinate hydrochloride
18650-39-0

(S)-methyl pipecolinate hydrochloride

C20H29NO6

C20H29NO6

Conditions
ConditionsYield
With 2-chloro-1-methyl-pyridinium iodide; triethylamine In dichloromethane at 12 - 25℃;

195202-08-5Relevant articles and documents

Synthetic process of homodimer of FKBP ligand

-

Paragraph 0030; 0044-0046, (2019/05/28)

The invention discloses a synthesis process of homodimer of FKBP ligand and belongs to an improved synthesis process of AP1903, wherein the homodimer of FKBP ligand refers to AP1903. According to theoptimized route of the synthesis process chooses, (S)-piperidine-2-methyl formate is connected to the compound Cpd9' as selected, an acid Cpd6' obtained after ester hydrolysis is easier to be purified by post-treatment purification, and precipitation or extraction treatment can be chosen by the post-treatment purification. Although the total reaction steps of the synthetic route in the prior literature are the same as the optimized route of the invention, the synthetic route in the prior literature belongs to the vertical route, and the post-treatment of the fifth, sixth and eighth steps requires column chromatography, thereby leading to a higher research and development cost. The optimized AP1903 synthetic route belongs to the parallel route, and the post-treatment is simpler and more advantageous for separation and purification, so that the cost of research and development is relatively low and the economic benefit is obviously superior to that of the synthetic route in the prior art.

METHODS AND COMPOSITIONS FOR THE SYNTHESIS OF MULTIMERIZING AGENTS

-

, (2012/08/08)

The invention features methods and compositions for the synthesis of multimerizing agents.

Synthetic multimerizing agents

-

, (2008/06/13)

New compounds are disclosed for multimerizing immunophilins and proteins containing immunophilin or immunophilin-related domains. The compounds are of the formulaM-L-Qwhere M is a synthetic ligand for an FKBP protein

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