149690-12-0

Basic information

• Product Name: (2R,4S)-ethyl 5-([1,1'-biphenyl]-4-yl)-4-aMino-2-Methylpentanoate
• Synonyms: (2R,4S)-ethyl 5-([1,1'-biphenyl]-4-yl)-4-aMino-2-Methylpentanoate HCl;LCZ696 Intermediate2;LCZ698;[1,1'-Biphenyl]-4-pentanoic acid, γ-amino-α-methyl-, ethyl ester, hydrochloride (1:1), (αR,γS)-;(2R,4S)-ethyl 5-([1,1'-biphenyl]-4-yl)-4-aMino-2-Methylpentanoate;(2R,4S)-ethyl 5-([1,1'-biphenyl]-4-yl)-4-aMino-2-Methylpentanoate hydrochloride;(2R,4S)-4-Amino-5-(biphenyl-4-yl)-2-methylpentanoic acid ethyl ester hydrochloride;(2R,4S)-4-Amino-5-(biphenyl-4-yl)-2-methylpentanoic acid ethyl ester hydrochloride (1:1)
• CAS NO: 149690-12-0
• Molecular Formula: C₂₀H₂₅NO₂*ClH
• Molecular Weight: 347.87894
• EINECS: -0
• Product Categories: LCZ696
• Mol File: 149690-12-0.mol
• Article Data: 27

Chemical Properties

• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• Stability: Hygroscopic
• CAS DataBase Reference: (2R,4S)-ethyl 5-([1,1'-biphenyl]-4-yl)-4-aMino-2-Methylpentanoate(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,4S)-ethyl 5-([1,1'-biphenyl]-4-yl)-4-aMino-2-Methylpentanoate(149690-12-0)
• EPA Substance Registry System: (2R,4S)-ethyl 5-([1,1'-biphenyl]-4-yl)-4-aMino-2-Methylpentanoate(149690-12-0)

Safety Data

• Hazardous Substances Data: 149690-12-0(Hazardous Substances Data)

Usage

Description

(2R,4S)-Ethyl 5-([1,1'-biphenyl]-4-yl)-4-aMino-2-Methylpentanoate, also known as (2R,4S)-4-Amino-5-(biphenyl-4-yl)-2-methylpentanoic Acid Ethyl Ester Hydrochloride, is an organic compound with a complex molecular structure. It is characterized by its chiral centers at the 2R and 4S positions, which give it unique properties and reactivity. (2R,4S)-ethyl 5-([1,1'-biphenyl]-4-yl)-4-aMino-2-Methylpentanoate is a key intermediate in the synthesis of various pharmaceuticals due to its versatile functional groups and structural features.

Uses

Used in Pharmaceutical Synthesis:
(2R,4S)-Ethyl 5-([1,1'-biphenyl]-4-yl)-4-aMino-2-Methylpentanoate is used as a reagent in the synthesis of LCZ696, an angiotensin II receptor and neprilysin receptor dual inhibitor. (2R,4S)-ethyl 5-([1,1'-biphenyl]-4-yl)-4-aMino-2-Methylpentanoate plays a crucial role in the development of novel cardiovascular drugs that can effectively manage hypertension and heart failure by targeting two distinct pathways simultaneously.
Used in the Preparation of Novel NEP Inhibitor Prodrugs:
In addition to its role in the synthesis of LCZ696, (2R,4S)-Ethyl 5-([1,1'-biphenyl]-4-yl)-4-aMino-2-Methylpentanoate is also utilized as a reagent in the preparation of novel NEP (neutral endopeptidase) inhibitor prodrugs. These prodrugs are designed to treat hypertension and cardiovascular diseases by inhibiting the NEP enzyme, which is involved in the regulation of blood pressure and the breakdown of certain peptides.
Used in the Development of Antihypertensive Agents:
The compound is further employed in the development of antihypertensive agents, which are essential for managing high blood pressure. By targeting the angiotensin II receptor and neprilysin receptor, these agents can help regulate blood pressure and reduce the risk of cardiovascular events.

Upstream product

• 1591-31-7 4-iodo-biphenyl 
• 64-17-5 ethanol 
• 2350-89-2 p-vinylbiphenyl 
• 61502-90-7 4-Biphenylacetaldehyde 
• 1038924-71-8 (2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-amino-2-methylpentanoic acid hydrochloride 
• 1012341-48-8 (2E,4R)-5-{[1,1'-biphenyl]-4-yl}-4-{[(tert-butoxy)carbonyl]amino}-2-methylpent-2-enoic acid 
• 1038924-76-3 (3R,5S)-5-biphenyl-4-ylmethyl-3-methyl-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 108-91-8 cyclohexylamine 
• 1038924-70-7 (3R,5S)-5-({[1,1'-biphenyl]-4-yl}methyl)-3-methylpyrrolidin-2-one 
• 5728-52-9 (4-biphenylyl)acetic acid 
• 31603-77-7 4-biphenylacetonitrile 

Downstream Products

• 1038925-00-6 (3S,5S)-5-biphenyl-4-ylmethyl-3-methylpyrrolidin-2-one 
• 1038924-70-7 (3R,5S)-5-({[1,1'-biphenyl]-4-yl}methyl)-3-methylpyrrolidin-2-one 
• 149690-05-1 α-ethyl (αR,γS)-γ-<(3-carboxy-1-oxopropyl)amino>-α-methyl<1,1'-biphenyl>-4-pentanoate monosodium salt 
• 1257265-87-4 5-[((1S,3R)-1-biphenyl-4-ylmethyl-3-carboxybutylcarbamoyl)methyl]furan-2-carboxylic acid 
• 1257265-86-3 (2R,4S)-5-biphenyl-4-yl-4-[(5-carboxymethylfuran-2-carbonyl)amino]-2-methylpentanoic acid 
• 149709-62-6 α-ethyl (αR,γS)-γ-<(3-carboxy-1-oxopropyl)amino>-α-methyl<1,1'-biphenyl>-4-pentanoate 
• 1257265-53-4 (2S,4S)-5-biphenyl-4-yl-4-((S)-3-carboxy-3-cyclohexyl-propionylamino)-2-methyl-pentanoic acid 
• 1257266-44-6 (2R,4S)-ethyl 5-(biphenyl-4-yl)-4-(2-methoxyoxazole-5-carboxamido)-2-methylpentanoate 
• 1257266-41-3 (2R,4S)-ethyl 5-(biphenyl-4-yl)-4-(2-methoxythiazole-5-carboxamido)-2-methylpentanoate 
• 1257265-54-5 C₃₁H₄₁NO₅ 
• 1257265-94-3 6-((1S,3R)-1-biphenyl-4-ylmethyl-3-carboxy-butylcarbamoyl)-2-ethoxy-pyrimidine-4-carboxylic acid 
• 1257265-62-5 (2R,4S)-5-biphenyl-4-yl-4-(3,5-difluoro-4-methoxybenzoylamino)-2-methylpentanoic acid ethyl ester 
• 1257265-93-2 6-((1S,3R)-1-biphenyl-4-ylmethyl-3-ethoxycarbonyl-butylcarbamoyl)-2-hydroxy-pyrimidine-4-carboxylic acid 
• 1257266-04-8 (2R,4S)-5-biphenyl-4-yl-2-methyl-4-[(pyridazine-4-carbonyl)-amino]-pentanoic acid 

Relevant articles and documents

Synthesis of a Precursor to Sacubitril Using Enabling Technologies

An efficient preparation of a precursor to the neprilysin inhibitor sacubitril is described. The convergent synthesis features a diastereoselective Reformatsky-type carbethoxyallylation and a rhodium-catalyzed stereoselective hydrogenation for installation of the two key stereocenters. Moreover, by integrating machine-assisted methods with batch processes, this procedure allows a safe and rapid production of the key intermediates which are promptly transformed to the target molecule (3·HCl) over 7 steps in 54% overall yield.

AMMONIUM CARBOXYLATE COMPOUND, CRYSTALLINE FORM, AMORPHOUS FORM AND PREPARATION METHOD THEREOF

The present disclosure belongs to the field of chemical synthesis, and in particular relates to an ammonium carboxylate compound, a crystalline form and an amorphous form, and a preparation method thereof. The present disclosure prepares the compound and the crystalline form I and its single crystal, amorphous form and crystalline form II thereof. The compound, the crystalline forms, the single crystal and the amorphous form can stably exist and exhibit good solid forms, suitable for medicine-making. Furthermore, these products possess high purity and less single impurity. Moreover, the preparation methods of the present disclosure are easy to implement due to the simple processes with mild reaction conditions, and could produce products of high yield and high purity without complex purification steps. Furthermore, the preparation methods may facilitate safety, environmental protection, and industrial production.

Post-treatment method of sacubitril valsartan sodium intermediate

The invention discloses a post-treatment method of a sacubitril valsartan sodium intermediate. According to the method, a proper acid-binding agent is adopted; by removing acidic substances in an intermediate 1 ((2R, 4S)-4-amino-5-biphenyl-4-yl-2-methyl ethyl valerate hydrochloride) crude product prepared by a thionyl chloride/ethanol system, a high purity intermediate 1 can be obtained; and the method is simple to operate, and overcomes the problem of corrosivity of instruments and devices caused by repeated reduced pressure concentration of n-heptane in the prior art. The post-treatment method provided by the invention is more beneficial to subsequent preparation of sacubitril valsartan sodium, and is suitable for large-scale industrial production.