3-Thiazolidinecarboxylic acid, 4-[[[(1R)-1-[[(cyclohexylmethyl)thio]methyl]-2-oxo-2-[[(4-phenoxyphenyl) methyl]amino]ethyl]amino]carbonyl]-, 1,1-dimethylethyl ester, (4R)-

Base Information

• Chemical Name: 3-Thiazolidinecarboxylic acid, 4-[[[(1R)-1-[[(cyclohexylmethyl)thio]methyl]-2-oxo-2-[[(4-phenoxyphenyl) methyl]amino]ethyl]amino]carbonyl]-, 1,1-dimethylethyl ester, (4R)-
• CAS No.: 219625-92-0
• Molecular Formula: C₃₂H₄₃N₃O₅S₂
• Molecular Weight: 613.843
• Mol file: 219625-92-0.mol

Synonyms:

Chemical Property of 3-Thiazolidinecarboxylic acid, 4-[[[(1R)-1-[[(cyclohexylmethyl)thio]methyl]-2-oxo-2-[[(4-phenoxyphenyl) methyl]amino]ethyl]amino]carbonyl]-, 1,1-dimethylethyl ester, (4R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-Thiazolidinecarboxylic acid, 4-[[[(1R)-1-[[(cyclohexylmethyl)thio]methyl]-2-oxo-2-[[(4-phenoxyphenyl) methyl]amino]ethyl]amino]carbonyl]-, 1,1-dimethylethyl ester, (4R)-

There total 5 articles about 3-Thiazolidinecarboxylic acid, 4-[[[(1R)-1-[[(cyclohexylmethyl)thio]methyl]-2-oxo-2-[[(4-phenoxyphenyl) methyl]amino]ethyl]amino]carbonyl]-, 1,1-dimethylethyl ester, (4R)- 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:

Cyclohexylmethyl bromide (2550-36-9) → (R)-4-[(R)-2-Cyclohexylmethylsulfanyl-1-(4-phenoxy-benzylcarbamoyl)-ethylcarbamoyl]-thiazolidine-3-carboxylic acid tert-butyl ester (219625-92-0)

Guidance literature:

Multi-step reaction with 5 steps

1: NaOH; Bu₄NI / ethanol; H₂O / 72 h

2: 621 g / NaOH; Bu₄NI / ethanol / 1 h

3: HOBt; EDC / CH₂Cl₂

4: HCl / dioxane / 20 °C

5: EDC; HOBt / CH₂Cl₂

With hydrogenchloride; sodium hydroxide; tetra-(n-butyl)ammonium iodide; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In 1,4-dioxane; ethanol; dichloromethane; water;

DOI:10.1016/S0968-0896(02)00558-8

Reference yield:

(2R)-2-(t-butoxycarbonylamino)-3-cyclohexylmethylthiopropanoic acid (219626-94-5) → (R)-4-[(R)-2-Cyclohexylmethylsulfanyl-1-(4-phenoxy-benzylcarbamoyl)-ethylcarbamoyl]-thiazolidine-3-carboxylic acid tert-butyl ester (219625-92-0)

Guidance literature:

Multi-step reaction with 3 steps

1: HOBt; EDC / CH₂Cl₂

2: HCl / dioxane / 20 °C

3: EDC; HOBt / CH₂Cl₂

With hydrogenchloride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In 1,4-dioxane; dichloromethane;

DOI:10.1016/S0968-0896(02)00558-8

Reference yield:

(R)-2-Amino-3-cyclohexylmethylsulfanyl-propionic acid (473421-00-0) → (R)-4-[(R)-2-Cyclohexylmethylsulfanyl-1-(4-phenoxy-benzylcarbamoyl)-ethylcarbamoyl]-thiazolidine-3-carboxylic acid tert-butyl ester (219625-92-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 621 g / NaOH; Bu₄NI / ethanol / 1 h

2: HOBt; EDC / CH₂Cl₂

3: HCl / dioxane / 20 °C

4: EDC; HOBt / CH₂Cl₂

With hydrogenchloride; sodium hydroxide; tetra-(n-butyl)ammonium iodide; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In 1,4-dioxane; ethanol; dichloromethane;

DOI:10.1016/S0968-0896(02)00558-8

upstream raw materials:

N-(tert-butoxycarbonyl)-(R)-thiazolidine-4-carboxylic acid

2-amino-3-cyclohexylmethylsulfanyl-N-(4-phenoxy-benzyl)-propionamide

Cyclohexylmethyl bromide

(2R)-2-(t-butoxycarbonylamino)-3-cyclohexylmethylthiopropanoic acid

Downstream raw materials:

(2R)-N-(4-phenoxybenzyl)-3-cyclohexylmethylthio-2-((4R)-thiazolidin-4-ylcarbonylamino)propanamide

Refernces

• 1、 Seko, Takuya,Kato, Masashi,Kohno, Hiroshi,Ono, Shizuka,Hashimura, Kazuya,Takimizu, Hideyuki,Nakai, Katsuhiko,Maegawa, Hitoshi,Katsube, Nobuo,Toda, Masaaki. "Structure-activity study of L-cysteine-based N-type calcium channel blockers: optimization of N- and C-terminal substituents.". . p. 915 - 918. Retrieved 2007/10/03.