4-[[(R)-1-(benzo[b]thiophene-3-carbonyl)-2-methylazetidine-2-carbonyl]-(3-chlorobenzyl)amino]butyric acid methyl ester

Base Information

Chemical Name:4-[[(R)-1-(benzo[b]thiophene-3-carbonyl)-2-methylazetidine-2-carbonyl]-(3-chlorobenzyl)amino]butyric acid methyl ester
CAS No.:1391078-75-3
Molecular Formula:C₂₆H₂₇ClN₂O₄S
Molecular Weight:499.03
Hs Code.:

Synonyms:4-[[(R)-1-(benzo[b]thiophene-3-carbonyl)-2-methylazetidine-2-carbonyl]-(3-chlorobenzyl)amino]butyric acid methyl ester

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Chemical Property of 4-[[(R)-1-(benzo[b]thiophene-3-carbonyl)-2-methylazetidine-2-carbonyl]-(3-chlorobenzyl)amino]butyric acid methyl ester

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Technology Process of 4-[[(R)-1-(benzo[b]thiophene-3-carbonyl)-2-methylazetidine-2-carbonyl]-(3-chlorobenzyl)amino]butyric acid methyl ester

There total 11 articles about 4-[[(R)-1-(benzo[b]thiophene-3-carbonyl)-2-methylazetidine-2-carbonyl]-(3-chlorobenzyl)amino]butyric acid methyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

: 5381-25-9
benzo[b]thiophene-3-carboxylic acid

: 1391078-19-5
4-[(3-chloro-benzyl)-((R)-2-methyl-azetidine-2-carbonyl)-amino]-butyric acid methyl ester hydrochloride

: 1391078-75-3
4-[[(R)-1-(benzo[b]thiophene-3-carbonyl)-2-methylazetidine-2-carbonyl]-(3-chlorobenzyl)amino]butyric acid methyl ester

Guidance literature:: benzo[b]thiophene-3-carboxylic acid; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; dichloromethane; at 20 ℃; for 15h;

4-[(3-chloro-benzyl)-((R)-2-methyl-azetidine-2-carbonyl)-amino]-butyric acid methyl ester hydrochloride; In tetrahydrofuran; dichloromethane; at 20 ℃; for 4.5h;

Reference yield: 87.0%

: 5381-25-9
benzo[b]thiophene-3-carboxylic acid

: (R)-2-[(3-chlorobenzyl)(3-methoxycarbonylpropyl)carbamoyl]-2-methylazetidine-1-carboxylic acid tert-butyl ester hydrochloride

: 1391078-75-3
4-[[(R)-1-(benzo[b]thiophene-3-carbonyl)-2-methylazetidine-2-carbonyl]-(3-chlorobenzyl)amino]butyric acid methyl ester

Guidance literature:: benzo[b]thiophene-3-carboxylic acid; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; dichloromethane; at 20 ℃; for 15h;

(R)-2-[(3-chlorobenzyl)(3-methoxycarbonylpropyl)carbamoyl]-2-methylazetidine-1-carboxylic acid tert-butyl ester hydrochloride; In tetrahydrofuran; dichloromethane; at 20 ℃; for 4.5h;
DOI:10.1021/jm5012885

Reference yield:

: 1391077-69-2
2-[benzyl-(2-chloroethyl)amino]propionic acid ethyl ester

: 1391078-75-3
4-[[(R)-1-(benzo[b]thiophene-3-carbonyl)-2-methylazetidine-2-carbonyl]-(3-chlorobenzyl)amino]butyric acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: potassium hexamethylsilazane / toluene; tetrahydrofuran / 2 h / -78 - 20 °C / Inert atmosphere

1.2: 0.17 h / 20 °C

2.1: hydrogen / palladium on activated charcoal / ethanol / 24 h / 20 °C / Inert atmosphere

3.1: sodium hydroxide; water / ethanol / 15 h / 20 °C

3.2: pH 5

4.1: chiralpak AD-H / hexane; ethanol; formic acid / 20 °C / Resolution of racemate

5.1: 1-chloro-1-(dimethylamino)-2-methyl-1-propene / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

5.2: 2.5 h / -5 - 20 °C

6.1: hydrogenchloride / 1,4-dioxane / 16 h / 20 °C / Inert atmosphere

7.1: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane; tetrahydrofuran / 15 h / 20 °C

7.2: 4.5 h / 20 °C

With hydrogenchloride; 1-chloro-1-(dimethylamino)-2-methyl-1-propene; water; hydrogen; potassium hexamethylsilazane; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; sodium hydroxide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; formic acid; ethanol; hexane; dichloromethane; toluene;