Cas no 84324-12-9 ((-)-N-1-(R)-Ethoxycarbonxyl-3-phenylpropyl-L-alanine)

(-)-N-1-(R)-Ethoxycarbonyl-3-phenylpropyl-L-alanine is a chiral intermediate widely used in the synthesis of pharmaceuticals, particularly ACE inhibitors. Its stereospecific structure ensures high enantiomeric purity, critical for the efficacy and safety of active pharmaceutical ingredients (APIs). The compound features an ethoxycarbonyl group and a phenylpropyl side chain, enhancing its utility in peptide coupling and asymmetric synthesis. Its well-defined configuration allows for precise control in complex synthetic pathways, reducing unwanted byproducts. This intermediate is valued for its compatibility with standard protecting group strategies and its role in producing biologically active molecules with improved pharmacokinetic profiles.
(-)-N-1-(R)-Ethoxycarbonxyl-3-phenylpropyl-L-alanine structure
84324-12-9 structure
Product Name:(-)-N-1-(R)-Ethoxycarbonxyl-3-phenylpropyl-L-alanine
CAS No:84324-12-9
MF:C15H21NO4
MW:279.33154463768
CID:989321
Update Time:2025-05-19

(-)-N-1-(R)-Ethoxycarbonxyl-3-phenylpropyl-L-alanine Chemical and Physical Properties

Names and Identifiers

    • (-)-N-[1-(R)-Ethoxycarbonxyl-3-phenylpropyl]-L-alanine
    • (-)-N-(1-R-ETHOXYCARBONXYL-3-PHENYLPROPYL)-S-ALANINE
    • N-<1(R)-(ethoxycarbonyl)-3-phenylpropyl>-(S)-alanine
    • 1-Ethyl (αR)-α-[[(1S)-1-carboxyethyl]amino]benzenebutanoate (ACI)
    • Benzenebutanoic acid, α-[(1-carboxyethyl)amino]-, monoethyl ester, [S-(R*,S*)]- (ZCI)
    • Benzenebutanoic acid, α-[[(1S)-1-carboxyethyl]amino]-, monoethyl ester, (αR)- (9CI)
    • N-[(R)-1-Ethoxycarbonyl-3-phenylpropyl]-L-alanine
    • (-)-N-1-(R)-Ethoxycarbonxyl-3-phenylpropyl-L-alanine
    • Inchi: 1S/C15H21NO4/c1-3-20-15(19)13(16-11(2)14(17)18)10-9-12-7-5-4-6-8-12/h4-8,11,13,16H,3,9-10H2,1-2H3,(H,17,18)/t11-,13+/m0/s1
    • InChI Key: CEIWXEQZZZHLDM-WCQYABFASA-N
    • SMILES: [C@@H](C(=O)OCC)(N[C@@H](C)C(=O)O)CCC1C=CC=CC=1

Experimental Properties

  • Melting Point: 145-147°C

(-)-N-1-(R)-Ethoxycarbonxyl-3-phenylpropyl-L-alanine Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
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(-)-N-1-(R)-Ethoxycarbonxyl-3-phenylpropyl-L-alanine Production Method

Production Method 1

Reaction Conditions
Reference
Substituted acyl derivatives of octahydro-1H-isoindole-1-carboxylic acids and esters
, European Patent Organization, , ,

Production Method 2

Reaction Conditions
1.1 Reagents: Trifluoroacetic acid Solvents: Trifluoroacetic acid
Reference
A practical and diastereoselective synthesis of angiotensin converting enzyme inhibitors
Iwasaki, Genji; et al, Chemical & Pharmaceutical Bulletin, 1989, 37(2), 280-3

Production Method 3

Reaction Conditions
Reference
Preparation of azobicyclooctanecarboxylates as psychotropic drugs
, Federal Republic of Germany, , ,

Production Method 4

Reaction Conditions
1.1 Reagents: Potassium carbonate Solvents: Nitromethane
2.1 Reagents: Trifluoroacetic acid Solvents: Trifluoroacetic acid
Reference
A practical and diastereoselective synthesis of angiotensin converting enzyme inhibitors
Iwasaki, Genji; et al, Chemical & Pharmaceutical Bulletin, 1989, 37(2), 280-3

Production Method 5

Reaction Conditions
1.1 Reagents: Triethylamine Solvents: Dichloromethane ;  24 h, rt
2.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol ;  24 h, rt
Reference
Synthesis of (R,S)-N-(1-Ethoxycarbonyl)-3-phenylpropyl-L-alanine
Fang, Yingquan, Zhongguo Yiyao Gongye Zazhi, 2013, 44(8), 749-751

Production Method 6

Reaction Conditions
Reference
N-Substituted glycine compounds
, Japan, , ,

Production Method 7

Reaction Conditions
1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol ;  24 h, rt
2.1 Reagents: Sulfuric acid Solvents: Ethanol ;  4 h, reflux
3.1 Solvents: Dichloromethane ;  -78 °C; 10 h, -78 °C
4.1 Reagents: Triethylamine Solvents: Dichloromethane ;  24 h, rt
5.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol ;  24 h, rt
Reference
Synthesis of (R,S)-N-(1-Ethoxycarbonyl)-3-phenylpropyl-L-alanine
Fang, Yingquan, Zhongguo Yiyao Gongye Zazhi, 2013, 44(8), 749-751

Production Method 8

Reaction Conditions
1.1 rt → 50 °C; 5 h, 50 °C
2.1 Reagents: Aluminum chloride ;  rt → reflux; 5 h, reflux
2.2 Reagents: Hydrochloric acid Solvents: Water ;  3 h, cooled
3.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol ;  24 h, rt
4.1 Reagents: Sulfuric acid Solvents: Ethanol ;  4 h, reflux
5.1 Solvents: Dichloromethane ;  -78 °C; 10 h, -78 °C
6.1 Reagents: Triethylamine Solvents: Dichloromethane ;  24 h, rt
7.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol ;  24 h, rt
Reference
Synthesis of (R,S)-N-(1-Ethoxycarbonyl)-3-phenylpropyl-L-alanine
Fang, Yingquan, Zhongguo Yiyao Gongye Zazhi, 2013, 44(8), 749-751

Production Method 9

Reaction Conditions
1.1 Reagents: Sodium cyanoborohydride Solvents: Ethanol ,  Acetic acid
Reference
Synthesis of tritium-labeled enalapril maleate
Bartroli, J.; et al, Journal of Labelled Compounds and Radiopharmaceuticals, 1986, 23(7), 771-6

Production Method 10

Reaction Conditions
1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol ;  24 h, rt
Reference
Synthesis of (R,S)-N-(1-Ethoxycarbonyl)-3-phenylpropyl-L-alanine
Fang, Yingquan, Zhongguo Yiyao Gongye Zazhi, 2013, 44(8), 749-751

Production Method 11

Reaction Conditions
Reference
N-Substituted glycine compounds
, Japan, , ,

Production Method 12

Reaction Conditions
Reference
Substituted acyl derivatives of octahydro-1H-isoindole-1-carboxylic acids and esters
, European Patent Organization, , ,

Production Method 13

Reaction Conditions
1.1 Reagents: Thionyl chloride Solvents: Ethanol
2.1 Reagents: Potassium carbonate Solvents: Acetonitrile
3.1 Reagents: Trifluoroacetic acid Solvents: Trifluoroacetic acid
Reference
A practical and diastereoselective synthesis of angiotensin converting enzyme inhibitors
Iwasaki, Genji; et al, Chemical & Pharmaceutical Bulletin, 1989, 37(2), 280-3

Production Method 14

Reaction Conditions
1.1 Solvents: Dichloromethane ;  -78 °C; 10 h, -78 °C
2.1 Reagents: Triethylamine Solvents: Dichloromethane ;  24 h, rt
3.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol ;  24 h, rt
Reference
Synthesis of (R,S)-N-(1-Ethoxycarbonyl)-3-phenylpropyl-L-alanine
Fang, Yingquan, Zhongguo Yiyao Gongye Zazhi, 2013, 44(8), 749-751

Production Method 15

Reaction Conditions
1.1 Reagents: Sulfuric acid Solvents: Ethanol ;  4 h, reflux
2.1 Solvents: Dichloromethane ;  -78 °C; 10 h, -78 °C
3.1 Reagents: Triethylamine Solvents: Dichloromethane ;  24 h, rt
4.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol ;  24 h, rt
Reference
Synthesis of (R,S)-N-(1-Ethoxycarbonyl)-3-phenylpropyl-L-alanine
Fang, Yingquan, Zhongguo Yiyao Gongye Zazhi, 2013, 44(8), 749-751

Production Method 16

Reaction Conditions
1.1 Reagents: Sodium nitrite ,  Sulfuric acid Solvents: Acetic acid ,  Water
1.2 Reagents: Sodium nitrite ,  Sulfuric acid ,  Potassium bromide
2.1 Reagents: Thionyl chloride Solvents: Ethanol
3.1 Reagents: Potassium carbonate Solvents: Acetonitrile
4.1 Reagents: Trifluoroacetic acid Solvents: Trifluoroacetic acid
Reference
A practical and diastereoselective synthesis of angiotensin converting enzyme inhibitors
Iwasaki, Genji; et al, Chemical & Pharmaceutical Bulletin, 1989, 37(2), 280-3

Production Method 17

Reaction Conditions
1.1 -
2.1 Reagents: Sodium nitrite ,  Sulfuric acid Solvents: Acetic acid ,  Water
2.2 Reagents: Sodium nitrite ,  Sulfuric acid ,  Potassium bromide
3.1 Reagents: Thionyl chloride Solvents: Ethanol
4.1 Reagents: Potassium carbonate Solvents: Acetonitrile
5.1 Reagents: Trifluoroacetic acid Solvents: Trifluoroacetic acid
Reference
A practical and diastereoselective synthesis of angiotensin converting enzyme inhibitors
Iwasaki, Genji; et al, Chemical & Pharmaceutical Bulletin, 1989, 37(2), 280-3

Production Method 18

Reaction Conditions
1.1 Solvents: Methanol ,  Water
2.1 -
3.1 Reagents: Sodium nitrite ,  Sulfuric acid Solvents: Acetic acid ,  Water
3.2 Reagents: Sodium nitrite ,  Sulfuric acid ,  Potassium bromide
4.1 Reagents: Thionyl chloride Solvents: Ethanol
5.1 Reagents: Potassium carbonate Solvents: Acetonitrile
6.1 Reagents: Trifluoroacetic acid Solvents: Trifluoroacetic acid
Reference
A practical and diastereoselective synthesis of angiotensin converting enzyme inhibitors
Iwasaki, Genji; et al, Chemical & Pharmaceutical Bulletin, 1989, 37(2), 280-3

Production Method 19

Reaction Conditions
1.1 Reagents: Aluminum chloride ;  rt → reflux; 5 h, reflux
1.2 Reagents: Hydrochloric acid Solvents: Water ;  3 h, cooled
2.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol ;  24 h, rt
3.1 Reagents: Sulfuric acid Solvents: Ethanol ;  4 h, reflux
4.1 Solvents: Dichloromethane ;  -78 °C; 10 h, -78 °C
5.1 Reagents: Triethylamine Solvents: Dichloromethane ;  24 h, rt
6.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol ;  24 h, rt
Reference
Synthesis of (R,S)-N-(1-Ethoxycarbonyl)-3-phenylpropyl-L-alanine
Fang, Yingquan, Zhongguo Yiyao Gongye Zazhi, 2013, 44(8), 749-751

(-)-N-1-(R)-Ethoxycarbonxyl-3-phenylpropyl-L-alanine Raw materials

(-)-N-1-(R)-Ethoxycarbonxyl-3-phenylpropyl-L-alanine Preparation Products

Additional information on (-)-N-1-(R)-Ethoxycarbonxyl-3-phenylpropyl-L-alanine

Professional Introduction to Compound with CAS No. 84324-12-9 and Product Name: (-)-N-1-(R)-Ethoxycarbonxyl-3-phenylpropyl-L-alanine

The compound with CAS No. 84324-12-9 and the product name (-)-N-1-(R)-Ethoxycarbonxyl-3-phenylpropyl-L-alanine represents a significant advancement in the field of chiral chemistry and pharmaceutical development. This compound, characterized by its unique stereochemical configuration, has garnered considerable attention due to its potential applications in the synthesis of novel therapeutic agents and fine chemicals.

In recent years, the demand for enantiomerically pure compounds has surged, driven by the need for more effective and selective pharmaceuticals. The structure of (-)-N-1-(R)-Ethoxycarbonxyl-3-phenylpropyl-L-alanine incorporates a chiral center at the L-alanine moiety, which is a critical feature for achieving high enantiomeric purity. This specificity is essential for optimizing pharmacokinetic properties, minimizing side effects, and enhancing overall therapeutic efficacy.

The synthesis of this compound involves sophisticated organic transformations, including stereoselective reactions that are pivotal in establishing the desired stereochemical configuration. The ethoxycarbonyl group at the N-position and the phenylpropyl side chain contribute to the compound's versatility, making it a valuable intermediate in the construction of more complex molecules. Advanced synthetic methodologies, such as asymmetric hydrogenation and enzymatic resolution, have been employed to ensure high yields and purity levels.

Recent research has highlighted the potential of derivatives of (-)-N-1-(R)-Ethoxycarbonxyl-3-phenylpropyl-L-alanine in addressing various therapeutic challenges. For instance, studies have demonstrated its utility in developing novel protease inhibitors, which are crucial for treating conditions such as cancer and infectious diseases. The phenylpropyl moiety, in particular, has been shown to enhance binding affinity to target enzymes, thereby improving drug potency.

The pharmaceutical industry has been increasingly leveraging chiral compounds like (-)-N-1-(R)-Ethoxycarbonxyl-3-phenylpropyl-L-alanine to develop next-generation therapeutics. These compounds often exhibit improved pharmacological profiles compared to their racemic counterparts, leading to better patient outcomes. The growing body of evidence supporting their efficacy has prompted further investigation into their mechanisms of action and potential applications.

In addition to pharmaceutical applications, this compound has shown promise in the field of materials science. Its unique structural features make it a suitable candidate for designing advanced polymers and functional materials with tailored properties. The ability to precisely control stereochemistry allows for the creation of materials with enhanced mechanical strength, thermal stability, and biocompatibility.

The regulatory landscape for enantiomerically pure compounds is evolving rapidly, with agencies increasingly emphasizing the importance of chirality in drug development. Manufacturers must adhere to stringent guidelines to ensure the safety and efficacy of these products. The synthesis and characterization of (-)-N-1-(R)-Ethoxycarbonxyl-3-phenylpropyl-L-alanine exemplify the rigorous standards being set in this area.

Future research directions may explore novel derivatives of this compound that could expand its therapeutic applications further. Innovations in synthetic chemistry could enable the production of even more complex chiral molecules, opening up new avenues for drug discovery. Collaborative efforts between academia and industry will be essential in translating these findings into tangible benefits for patients worldwide.

The compound's role in advancing synthetic methodologies cannot be overstated. It serves as a benchmark for developing new synthetic routes that are efficient, scalable, and environmentally sustainable. As green chemistry principles gain prominence, compounds like (-)-N-1-(R)-Ethoxycarbonxyl-3-phenylpropyl-L-alanine will play a crucial role in reducing the environmental impact of chemical manufacturing processes.

In conclusion, (-)-N-1-(R)-Ethoxycarbonxyl-3-phenylpropyl-L-alanine represents a significant contribution to modern chemistry and pharmacology. Its unique structural features and versatile applications make it a valuable asset in both academic research and industrial development. As our understanding of chirality continues to grow, compounds like this will undoubtedly play an increasingly important role in shaping the future of medicine and materials science.

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