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

Base Information

• Chemical Name: methyl N-[(2S)-1-[(2R,3R)-3-hydroxy-2-{5-[4-(4-{2-[(2S)-1-[(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl]pyrrolidin-2-yl]-1H-imidazol-5-yl}phenyl)phenyl]-1H-imidazol-2-yl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamate
• CAS No.: 1416037-82-5
• Molecular Formula: C₄₀H₅₀N₈O₇
• Molecular Weight: 754.886

Synonyms:

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

Chemical Property:

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

There total 5 articles about methyl N-[(2S)-1-[(2R,3R)-3-hydroxy-2-{5-[4-(4-{2-[(2S)-1-[(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl]pyrrolidin-2-yl]-1H-imidazol-5-yl}phenyl)phenyl]-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:

α-amino-4-bromoacetophenone hydrochloride (5467-72-1) → methyl N-[(2S)-1-[(2R,3R)-3-hydroxy-2-{5-[4-(4-{2-[(2S)-1-[(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl]pyrrolidin-2-yl]-1H-imidazol-5-yl}phenyl)phenyl]-1H-imidazol-2-yl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamate (1416037-82-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 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 / 3 h / 20 °C

2: ammonium acetate / para-xylene / 1.5 h / 140 °C / Sealed tube

3: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydrogencarbonate / water; Dimethyl ether / 16 h / 95 °C / Sealed tube

4: hydrogenchloride / dichloromethane; water; 1,4-dioxane / 3 h / 20 °C

5: 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 / 3.5 h / 20 °C

With hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; ammonium acetate; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In 1,4-dioxane; Dimethyl ether; dichloromethane; para-xylene; water; N,N-dimethyl-formamide;

DOI:10.1124/dmd.115.068866

Reference yield:

(2S,3R)-1-[(tert-butoxy)carbonyl]-3-hydroxypyrrolidine-2-carboxylic acid (186132-96-7,335280-19-8) → methyl N-[(2S)-1-[(2R,3R)-3-hydroxy-2-{5-[4-(4-{2-[(2S)-1-[(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl]pyrrolidin-2-yl]-1H-imidazol-5-yl}phenyl)phenyl]-1H-imidazol-2-yl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamate (1416037-82-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 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 / 3 h / 20 °C

2: ammonium acetate / para-xylene / 1.5 h / 140 °C / Sealed tube

3: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydrogencarbonate / water; Dimethyl ether / 16 h / 95 °C / Sealed tube

4: hydrogenchloride / dichloromethane; water; 1,4-dioxane / 3 h / 20 °C

5: 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 / 3.5 h / 20 °C

With hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; ammonium acetate; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In 1,4-dioxane; Dimethyl ether; dichloromethane; para-xylene; water; N,N-dimethyl-formamide;

DOI:10.1124/dmd.115.068866

Reference yield:

(2S,3R)-tert-butyl 2-((2-(4-bromophenyl)-2-oxoethyl)carbamoyl)-3-hydroxypyrrolidine-1-carboxylate → methyl N-[(2S)-1-[(2R,3R)-3-hydroxy-2-{5-[4-(4-{2-[(2S)-1-[(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl]pyrrolidin-2-yl]-1H-imidazol-5-yl}phenyl)phenyl]-1H-imidazol-2-yl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamate (1416037-82-5)

Guidance literature:

Multi-step reaction with 4 steps

1: ammonium acetate / para-xylene / 1.5 h / 140 °C / Sealed tube

2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydrogencarbonate / water; Dimethyl ether / 16 h / 95 °C / Sealed tube

3: hydrogenchloride / dichloromethane; water; 1,4-dioxane / 3 h / 20 °C

4: 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 / 3.5 h / 20 °C

With hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; ammonium acetate; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In 1,4-dioxane; Dimethyl ether; dichloromethane; para-xylene; water; N,N-dimethyl-formamide;

DOI:10.1124/dmd.115.068866

upstream raw materials:

α-amino-4-bromoacetophenone hydrochloride

(2S,3R)-1-[(tert-butoxy)carbonyl]-3-hydroxypyrrolidine-2-carboxylic acid

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