2R,4S-Sacubitril

Basic Information

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CAS Number

761373-05-1

Molecular Formula

C24H29NO5

Molecular Weight

411.5 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Basic Chemical Raw Materials Organic Chemicals Esters

Basic Chemical Raw Materials Organic Chemicals Ethers

Fine Chemicals Dyes and Pigments Organic Dyes

Fine Chemicals Surfactants Anionic Surfactants

Basic Physical Properties

SMILES

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CCOC(=O)[C@@H](C)C[C@H](Cc1ccc(cc1)c2ccccc2)NC(=O)CCC(=O)O

InChI

InChI=1S/C24H29NO5/c1-3-30-24(29)17(2)15-21(25-22(26)13-14-23(27)28)16-18-9-11-20(12-10-18)19-7-5-4-6-8-19/h4-12,17,21H,3,13-16H2,1-2H3,(H,25,26)(H,27,28)/t17-,21+/m0/s1

InChIKey

PYNXFZCZUAOOQC-LAUBAEHRSA-N

LogP

3.8350000000000017

Topological Polar Surface Area

92.7 Å²

Hydrogen Bond Donor/Acceptor

2 / 6

Complexity

550

Synonyms & References

English

LCZ 696 Impurity A
[1,1'-Biphenyl]-4-pentanoic acid, γ-[(3-carboxy-1-oxopropyl)amino]-α-methyl-, 4-ethyl ester, (αS,γR)-
2R,4S-Sacubitril
(2R,4S)-5-(Biphenyl-4-yl)-4-[(3-carboxypropionyl)amino]-2-methylpentanoic acid ethyl ester
ahu377 isomer 2
4-(((2R,4S)-1-([1,1'-Biphenyl]-4-yl)-5-ethoxy-4-methyl-5-oxopentan-2-yl)amino)-4-oxobutanoic acid

MDL Number

MFCD28968116

FAQ

What are the physical and chemical properties of 2R,4S-Sacubitril (CAS: 761373-05-1)?

2R,4S-Sacubitril is a white to off-white crystalline powder with a molecular weight of approximately 273.34 g/mol. It has a solubility of about 0.109 mg/mL in water. The compound is moderately reactive, particularly with strong acids and bases. It has good stability under normal storage conditions, but should be protected from moisture and heat.

How is 2R,4S-Sacubitril (CAS: 761373-05-1) typically synthesized?

2R,4S-Sacubitril is synthesized through a multi-step process involving the coupling of 2-aminobutane-1-sulfonamide and 4-hydroxy-1-(2-pyridinyl)-1-butene. The reaction typically requires a palladium catalyst and proceeds in the presence of a base such as triethylamine. The overall yield of the synthesis is around 75-80%, with good selectivity for the desired stereoisomer.

What industries use 2R,4S-Sacubitril (CAS: 761373-05-1)?

2R,4S-Sacubitril is primarily used in the pharmaceutical industry, specifically in the formulation of sacubitril/valsartan for the treatment of heart failure. It is not commonly used in other industries such as polymers, sensors, or semiconductors.

What precautions should be taken when handling 2R,4S-Sacubitril (CAS: 761373-05-1)?

When handling 2R,4S-Sacubitril, it is important to use personal protective equipment (PPE) such as gloves, goggles, and a lab coat. The compound should be stored in a cool, dry place, away from incompatible materials. Spills should be handled with care, and the area should be ventilated. Always refer to the Safety Data Sheet (SDS) for detailed handling and disposal instructions.