(R,E)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpent-2-enoic acid

Base Information

• Chemical Name: (R,E)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpent-2-enoic acid
• CAS No.: 1012341-48-8
• Molecular Formula: C23H27NO4
• Molecular Weight: 381.472
• Mol file: 1012341-48-8.mol

Synonyms:(R,E)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpent-2-enoic acid;(2E,4R)-5-[1,1'-biphenyl]-4-yl-4-[[(1,1-dimethylethoxy)carbonyl]amino]-2-methyl-2-Pentenoic acid;5-Biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methyl-pent-2-enoic acid;2-Pentenoic acid, 5-[1,1'-biphenyl]-4-yl-4-[[(1,1-dimethylethoxy)carbonyl]amino]-2-methyl-, (2E,4R)-

Chemical Property of (R,E)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpent-2-enoic acid

Chemical Property:

• Vapor Pressure: 8.4-839.931Pa at 20℃
• Boiling Point: 595.6±50.0 °C(Predicted)
• PKA: 4.67±0.19(Predicted)
• PSA: 75.63000
• Density: 1.132±0.06 g/cm3(Predicted)
• LogP: 5.21120
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

99.9% ^*data from raw suppliers

(R,E)-5-([1,1-Biphenyl]-4-yl)-4-((tert-butoxycarbonyl)amino)-2-methylpent-2-enoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (R,E)-5-([1,1-Biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-methylpent-2-enoic Acid is used in preparation of sacubitril intermediate using Nickel Salt catalyst.

Technology Process of (R,E)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpent-2-enoic acid

There total 6 articles about (R,E)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpent-2-enoic 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: 70.0%

ethyl 5-(4-<1,1'-biphenyl>yl)-4-<<(1,1-dimethylethoxy)carbonyl>amino>-2-methyl-2-pentenoate (149709-59-1) → (2E,4R)-5-{[1,1'-biphenyl]-4-yl}-4-{[(tert-butoxy)carbonyl]amino}-2-methylpent-2-enoic acid (1012341-48-8)

Guidance literature:

With ethanol; lithium hydroxide; at 35 ℃; for 1h;

Reference yield:

(R)-5-biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methylenepentanoic acid (1174130-80-3) → (2E,4R)-5-{[1,1'-biphenyl]-4-yl}-4-{[(tert-butoxy)carbonyl]amino}-2-methylpent-2-enoic acid (1012341-48-8)

Guidance literature:

With sodium hydrogencarbonate; triphenylphosphine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In xylene; Reflux;

Reference yield:

N-[(1R)-2-[1,1'-biphenyl]-4-yl-1-(hydroxymethyl)ethyl]carbamic acid tert-butyl ester (1426129-50-1) → (2E,4R)-5-{[1,1'-biphenyl]-4-yl}-4-{[(tert-butoxy)carbonyl]amino}-2-methylpent-2-enoic acid (1012341-48-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium bromide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / Isopropyl acetate / 0.5 h / 20 °C

1.2: 1.33 h / 10 - 15 °C

2.1: 1 h / 30 °C

3.1: lithium hydroxide / 1 h / 80 °C

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium bromide; lithium hydroxide; In Isopropyl acetate;

upstream raw materials:

ethyl 5-(4-<1,1'-biphenyl>yl)-4-<<(1,1-dimethylethoxy)carbonyl>amino>-2-methyl-2-pentenoate

(R)-5-biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methylenepentanoic acid

N-[(1R)-2-[1,1'-biphenyl]-4-yl-1-(hydroxymethyl)ethyl]carbamic acid tert-butyl ester

methyl (R)-3-(4-bromophenyl)-2-((tert-butoxycarbonyl)amino)propanoate

Downstream raw materials:

(2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid

(2S,4S)-5-biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methylpentanoic acid

(2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-amino-2-methylpentanoic acid ethyl ester hydrochloride

α-ethyl (αR,γS)-γ-<(3-carboxy-1-oxopropyl)amino>-α-methyl<1,1'-biphenyl>-4-pentanoate

Refernces

• 1、 -. "Method for preparing LCZ-696 key intermediate". Paragraph 0039; 0045; 0051; 0057. . Retrieved 2017/03/25.
• 2、 -. "Preparation method of sacubitril intermediate having low triphenylphosphine oxide content". Paragraph 0011. . Retrieved 2017/10/12.