methyl {(2S)-1-[(2S)-2-{4-[2-(4-{2-[(2S)-1-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}pyrrolidin-2-yl]-1H-benzimidazol-5-yl}phenyl)pyrimidin-5-yl]-1H-imidazol-2-yl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl}carbamate

Base Information

• Chemical Name: methyl {(2S)-1-[(2S)-2-{4-[2-(4-{2-[(2S)-1-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}pyrrolidin-2-yl]-1H-benzimidazol-5-yl}phenyl)pyrimidin-5-yl]-1H-imidazol-2-yl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl}carbamate
• CAS No.: 1352212-17-9
• Molecular Formula: C₄₂H₅₀N₁₀O₆
• Molecular Weight: 790.922

Synonyms:methyl {(2S)-1-[(2S)-2-{4-[2-(4-{2-[(2S)-1-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}pyrrolidin-2-yl]-1H-benzimidazol-5-yl}phenyl)pyrimidin-5-yl]-1H-imidazol-2-yl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl}carbamate

Chemical Property of methyl {(2S)-1-[(2S)-2-{4-[2-(4-{2-[(2S)-1-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}pyrrolidin-2-yl]-1H-benzimidazol-5-yl}phenyl)pyrimidin-5-yl]-1H-imidazol-2-yl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl}carbamate

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Technology Process of methyl {(2S)-1-[(2S)-2-{4-[2-(4-{2-[(2S)-1-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}pyrrolidin-2-yl]-1H-benzimidazol-5-yl}phenyl)pyrimidin-5-yl]-1H-imidazol-2-yl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl}carbamate

There total 13 articles about methyl {(2S)-1-[(2S)-2-{4-[2-(4-{2-[(2S)-1-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}pyrrolidin-2-yl]-1H-benzimidazol-5-yl}phenyl)pyrimidin-5-yl]-1H-imidazol-2-yl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl}carbamate 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:

2-[(2S)-pyrrolidin-2-yl]-5-[4-(5-{2-[(2S)-pyrrolidin-2-yl]-1H-imidazol-5-yl}pyrimidin-2-yl)phenyl]-1H-benzimidazole hydrochloride + N-methoxycarbonyl-L-valine (111398-44-8,74761-42-5) → methyl {(2S)-1-[(2S)-2-{4-[2-(4-{2-[(2S)-1-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}pyrrolidin-2-yl]-1H-benzimidazol-5-yl}phenyl)pyrimidin-5-yl]-1H-imidazol-2-yl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl}carbamate (1352212-17-9)

Guidance literature:

N-methoxycarbonyl-L-valine; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In acetonitrile; at 20 ℃; for 0.333333h;

2-[(2S)-pyrrolidin-2-yl]-5-[4-(5-{2-[(2S)-pyrrolidin-2-yl]-1H-imidazol-5-yl}pyrimidin-2-yl)phenyl]-1H-benzimidazole hydrochloride; With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20 ℃; for 18h;

Reference yield:

N-(tert-butoxycarbonyl)-L-prolinol (69610-40-8) → methyl {(2S)-1-[(2S)-2-{4-[2-(4-{2-[(2S)-1-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}pyrrolidin-2-yl]-1H-benzimidazol-5-yl}phenyl)pyrimidin-5-yl]-1H-imidazol-2-yl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl}carbamate (1352212-17-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: sodium hydrogencarbonate; sodium hypochlorite; sodium bromide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / water / 0 - 90 °C

2.1: ammonia / water; methanol / 19.17 h / 20 °C / Cooling with ice

3.1: sodium hydride / tetrahydrofuran; mineral oil / 0.33 h / 0 °C

3.2: 16 h / 20 °C

4.1: N-Bromosuccinimide / dichloromethane; acetonitrile / 2 h / 20 °C

5.1: TurboGrignard / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

5.2: 16 h / 20 °C

6.1: potassium phosphate / tricyclohexylphosphine; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / cyclopentyl methyl ether / 16 h / 110 °C

7.1: hydrogenchloride / 1,4-dioxane; ethanol / 3 h / 70 °C

8.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / acetonitrile / 0.33 h / 20 °C

8.2: 18 h / 20 °C

With hydrogenchloride; sodium hypochlorite; potassium phosphate; N-Bromosuccinimide; TurboGrignard; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; ammonia; sodium hydride; sodium hydrogencarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium bromide; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tricyclohexylphosphine; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; cyclopentyl methyl ether; water; acetonitrile; mineral oil;

Reference yield:

(S)-tert-butyl 2-(1H-imidazol-2-yl)pyrrolidine-1-carboxylate (1007882-58-7,1332326-40-5) → methyl {(2S)-1-[(2S)-2-{4-[2-(4-{2-[(2S)-1-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}pyrrolidin-2-yl]-1H-benzimidazol-5-yl}phenyl)pyrimidin-5-yl]-1H-imidazol-2-yl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl}carbamate (1352212-17-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.33 h / 0 °C

1.2: 16 h / 20 °C

2.1: N-Bromosuccinimide / dichloromethane; acetonitrile / 2 h / 20 °C

3.1: TurboGrignard / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

3.2: 16 h / 20 °C

4.1: potassium phosphate / tricyclohexylphosphine; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / cyclopentyl methyl ether / 16 h / 110 °C

5.1: hydrogenchloride / 1,4-dioxane; ethanol / 3 h / 70 °C

6.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / acetonitrile / 0.33 h / 20 °C

6.2: 18 h / 20 °C

With hydrogenchloride; potassium phosphate; N-Bromosuccinimide; TurboGrignard; sodium hydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tricyclohexylphosphine; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; cyclopentyl methyl ether; acetonitrile; mineral oil;

upstream raw materials:

N-(tert-butoxycarbonyl)-L-prolinol

Boc-L-Pro-H

N-methoxycarbonyl-L-valine

L-valine

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