(S)-2′-(3′-(4-((2-amino-4-(((tert-butoxy)carbonyl)amino)butanamido)methyl)-[2,4′-bioxazol]-2′-yl)-[1,1′-biphenyl]-3-yl)-[2,4′-bioxazol]-4-carboxylic acid

Base Information

Chemical Name:(S)-2′-(3′-(4-((2-amino-4-(((tert-butoxy)carbonyl)amino)butanamido)methyl)-[2,4′-bioxazol]-2′-yl)-[1,1′-biphenyl]-3-yl)-[2,4′-bioxazol]-4-carboxylic acid
CAS No.:1447424-78-3
Molecular Formula:C₃₅H₃₃N₇O₉
Molecular Weight:695.689
Hs Code.:

Synonyms:(S)-2′-(3′-(4-((2-amino-4-(((tert-butoxy)carbonyl)amino)butanamido)methyl)-[2,4′-bioxazol]-2′-yl)-[1,1′-biphenyl]-3-yl)-[2,4′-bioxazol]-4-carboxylic acid

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Chemical Property of (S)-2′-(3′-(4-((2-amino-4-(((tert-butoxy)carbonyl)amino)butanamido)methyl)-[2,4′-bioxazol]-2′-yl)-[1,1′-biphenyl]-3-yl)-[2,4′-bioxazol]-4-carboxylic acid

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Technology Process of (S)-2′-(3′-(4-((2-amino-4-(((tert-butoxy)carbonyl)amino)butanamido)methyl)-[2,4′-bioxazol]-2′-yl)-[1,1′-biphenyl]-3-yl)-[2,4′-bioxazol]-4-carboxylic acid

There total 15 articles about (S)-2′-(3′-(4-((2-amino-4-(((tert-butoxy)carbonyl)amino)butanamido)methyl)-[2,4′-bioxazol]-2′-yl)-[1,1′-biphenyl]-3-yl)-[2,4′-bioxazol]-4-carboxylic acid 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: 100.0%

: 1447274-29-4
methyl (S)-2'-(3'-(4-((2-amino-4-(((t-butoxy)carbonyl)amino)butanamido)methyl)-[2,4'-bioxazol]-2'-yl)-[1,1'-biphenyl]-3-yl)-[2,4'-bioxazol]-4-carboxylate

: 1447424-78-3
(S)-2′-(3′-(4-((2-amino-4-(((tert-butoxy)carbonyl)amino)butanamido)methyl)-[2,4′-bioxazol]-2′-yl)-[1,1′-biphenyl]-3-yl)-[2,4′-bioxazol]-4-carboxylic acid

Guidance literature:: With lithium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 4h; Inert atmosphere;
DOI:10.1016/j.bmc.2013.05.033

Reference yield:

: 1711-09-7
3-bromobenzoyl chloride

: 1447424-78-3
(S)-2′-(3′-(4-((2-amino-4-(((tert-butoxy)carbonyl)amino)butanamido)methyl)-[2,4′-bioxazol]-2′-yl)-[1,1′-biphenyl]-3-yl)-[2,4′-bioxazol]-4-carboxylic acid

Guidance literature:: Multi-step reaction with 10 steps

1.1: triethylamine / dichloromethane / 20 °C / Inert atmosphere

2.1: pyridine hydrogenfluoride / tetrahydrofuran; pyridine / 18 h / 20 °C / Inert atmosphere

3.1: diethylamino-sulfur trifluoride / dichloromethane / 3 h / -78 °C / Inert atmosphere

3.2: -78 - 20 °C / Inert atmosphere

4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; Bromotrichloromethane / dichloromethane / 20 °C / Inert atmosphere

5.1: potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / toluene / 95 °C / Inert atmosphere

6.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; caesium carbonate / water; 1,4-dioxane / 4 h / 90 °C / Inert atmosphere

7.1: trifluoroacetic acid / dichloromethane / 3 h / 0 °C / Inert atmosphere

8.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.08 h / Inert atmosphere

8.2: 20 °C / Inert atmosphere

9.1: piperidine / acetonitrile / 3 h / 20 °C / Inert atmosphere

10.1: lithium hydroxide / tetrahydrofuran; water / 4 h / 20 °C / Inert atmosphere

With piperidine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; Bromotrichloromethane; diethylamino-sulfur trifluoride; potassium carbonate; benzotriazol-1-ol; caesium carbonate; pyridine hydrogenfluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; lithium hydroxide; In tetrahydrofuran; 1,4-dioxane; pyridine; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 6.1: |Suzuki Coupling;
DOI:10.1016/j.bmc.2013.05.033

Reference yield:

: 1447274-00-1
methyl 2-(1-(3-bromobenzamido)-2-((triisopropylsilyl)oxy)ethyl)oxazole-4-carboxylate

: 1447424-78-3
(S)-2′-(3′-(4-((2-amino-4-(((tert-butoxy)carbonyl)amino)butanamido)methyl)-[2,4′-bioxazol]-2′-yl)-[1,1′-biphenyl]-3-yl)-[2,4′-bioxazol]-4-carboxylic acid

Guidance literature:: Multi-step reaction with 12 steps

1.1: pyridine hydrogenfluoride / tetrahydrofuran; pyridine / 18 h / 20 °C / Inert atmosphere

2.1: diethylamino-sulfur trifluoride / dichloromethane / 3 h / -78 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; Bromotrichloromethane / dichloromethane / 20 °C / Inert atmosphere

4.1: lithium borohydride / tetrahydrofuran; ethanol / 0 - 20 °C / Inert atmosphere

5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; diphenyl phosphoryl azide / tetrahydrofuran / 18 h / 0 - 20 °C / Inert atmosphere

6.1: polymer-bound triphenylphosphine / tetrahydrofuran; water / 20 °C / Inert atmosphere

7.1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

8.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; caesium carbonate / water; 1,4-dioxane / 4 h / 90 °C / Inert atmosphere

9.1: trifluoroacetic acid / dichloromethane / 3 h / 0 °C / Inert atmosphere

10.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.08 h / Inert atmosphere

10.2: 20 °C / Inert atmosphere

11.1: piperidine / acetonitrile / 3 h / 20 °C / Inert atmosphere

12.1: lithium hydroxide / tetrahydrofuran; water / 4 h / 20 °C / Inert atmosphere

With piperidine; lithium borohydride; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; Bromotrichloromethane; diethylamino-sulfur trifluoride; diphenyl phosphoryl azide; benzotriazol-1-ol; caesium carbonate; pyridine hydrogenfluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; lithium hydroxide; In tetrahydrofuran; 1,4-dioxane; pyridine; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 8.1: |Suzuki Coupling;
DOI:10.1016/j.bmc.2013.05.033