{(E)-(1S,2S)-1-((S)-3-Fluoro-pyrrolidine-1-carbonyl)-2-[3'-(1H-tetrazol-5-yl)-biphenyl-4-yl]-pent-3-enyl}-carbamic acid tert-butyl ester

Base Information

• Chemical Name: {(E)-(1S,2S)-1-((S)-3-Fluoro-pyrrolidine-1-carbonyl)-2-[3'-(1H-tetrazol-5-yl)-biphenyl-4-yl]-pent-3-enyl}-carbamic acid tert-butyl ester
• CAS No.: 860779-32-4
• Molecular Formula: C₂₈H₃₃FN₆O₃
• Molecular Weight: 520.607
• Mol file: 860779-32-4.mol

Synonyms:

Chemical Property of {(E)-(1S,2S)-1-((S)-3-Fluoro-pyrrolidine-1-carbonyl)-2-[3'-(1H-tetrazol-5-yl)-biphenyl-4-yl]-pent-3-enyl}-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(E)-(1S,2S)-1-((S)-3-Fluoro-pyrrolidine-1-carbonyl)-2-[3'-(1H-tetrazol-5-yl)-biphenyl-4-yl]-pent-3-enyl}-carbamic acid tert-butyl ester

There total 2 articles about {(E)-(1S,2S)-1-((S)-3-Fluoro-pyrrolidine-1-carbonyl)-2-[3'-(1H-tetrazol-5-yl)-biphenyl-4-yl]-pent-3-enyl}-carbamic acid tert-butyl 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:

(βS)-4-bromo-N-(tert-butoxycarbonyl)-β-[(1E)-prop-1-en-1-yl]-L-phenylalanine (690258-03-8) → {(E)-(1S,2S)-1-((S)-3-Fluoro-pyrrolidine-1-carbonyl)-2-[3'-(1H-tetrazol-5-yl)-biphenyl-4-yl]-pent-3-enyl}-carbamic acid tert-butyl ester (860779-32-4)

Guidance literature:

Multi-step reaction with 2 steps

1: EDC; HOBt; DIEA / CH₂Cl₂

2: Pd(dppf)2Cl₂; aq. Na₂CO₃ / toluene; ethanol / Heating

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; In ethanol; dichloromethane; toluene; 2: Suzuki coupling;

DOI:10.1016/j.bmcl.2005.04.028

Reference yield:

(3S)-1-[(2S,3S,4E)-3-(4-bromophenyl)-2-(tert-butoxycarbonylamino)hex-4-enoyl]-3-fluoropyrrolidine (705292-97-3) + (3-(1H-tetrazol-5-yl)phenyl)boronic acid (775351-30-9) → {(E)-(1S,2S)-1-((S)-3-Fluoro-pyrrolidine-1-carbonyl)-2-[3'-(1H-tetrazol-5-yl)-biphenyl-4-yl]-pent-3-enyl}-carbamic acid tert-butyl ester (860779-32-4)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In ethanol; toluene; Heating;

DOI:10.1016/j.bmcl.2005.04.028

Reference yield:

{(E)-(1S,2S)-1-((S)-3-Fluoro-pyrrolidine-1-carbonyl)-2-[3'-(1H-tetrazol-5-yl)-biphenyl-4-yl]-pent-3-enyl}-carbamic acid tert-butyl ester (860779-32-4) → {1-(3-fluoro-pyrrolidine-1-carbonyl)-3-oxo-2-[3'-(1H-tetrazol-5-yl)-biphenyl-4-yl]-propyl}-carbamic acid tert-butyl ester (860779-40-4)

Guidance literature:

{(E)-(1S,2S)-1-((S)-3-Fluoro-pyrrolidine-1-carbonyl)-2-[3'-(1H-tetrazol-5-yl)-biphenyl-4-yl]-pent-3-enyl}-carbamic acid tert-butyl ester; With ozone; In methanol; dichloromethane;

With dimethylsulfide; In methanol; dichloromethane;

DOI:10.1016/j.bmcl.2005.04.028

upstream raw materials:

(3S)-1-[(2S,3S,4E)-3-(4-bromophenyl)-2-(tert-butoxycarbonylamino)hex-4-enoyl]-3-fluoropyrrolidine

(3-(1H-tetrazol-5-yl)phenyl)boronic acid

(βS)-4-bromo-N-(tert-butoxycarbonyl)-β-[(1E)-prop-1-en-1-yl]-L-phenylalanine

Downstream raw materials:

{1-(3-fluoro-pyrrolidine-1-carbonyl)-3-oxo-2-[3'-(1H-tetrazol-5-yl)-biphenyl-4-yl]-propyl}-carbamic acid tert-butyl ester

3-tert-butoxycarbonylamino-4-(3-fluoro-pyrrolidin-1-yl)-4-oxo-2-[3'-(1H-tetrazol-5-yl)-biphenyl-4-yl]-butyric acid