270596-51-5

Basic information

• Product Name: BOC-(S)-3-AMINO-4-(3-FLUOROPHENYL)BUTYRIC ACID
• Synonyms: N-BETA-T-BUTOXYCARBONYL-L-HOMO-(3-FLUOROPHENYL)ALANINE;N-T-BUTOXYCARBONYL-(S)-3-AMINO-4-(3-FLUOROPHENYL)BUTANOIC ACID;RARECHEM AK PT B067;BOC-3-FLUORO-L-BETA-HOMOPHENYLALANINE;BOC-BETA-HOPHE(3-F)-OH;BOC-PHE(3-F)-(C*CH2)OH;BOC-(S)-3-AMINO-4-(3-FLUOROPHENYL)BUTANOIC ACID;BOC-(S)-3-AMINO-4-(3-FLUOROPHENYL)BUTYRIC ACID
• CAS NO: 270596-51-5
• Molecular Formula: C15H20FNO4
• Molecular Weight: 297.32
• Product Categories: 3-Amino-4-phenylbutyric Acid Analogs;3-Amino-4-phenylbutanoic Acid Analogs;B-Amino
• Mol File: 270596-51-5.mol

Chemical Properties

• Boiling Point: 443.3 °C at 760 mmHg
• Flash Point: 221.9 °C
• Appearance: /
• Density: 1.192 g/cm³
• Vapor Pressure: 1.22E-08mmHg at 25°C
• Refractive Index: 1.514
• Storage Temp.: 2-8°C
• CAS DataBase Reference: BOC-(S)-3-AMINO-4-(3-FLUOROPHENYL)BUTYRIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-(S)-3-AMINO-4-(3-FLUOROPHENYL)BUTYRIC ACID(270596-51-5)
• EPA Substance Registry System: BOC-(S)-3-AMINO-4-(3-FLUOROPHENYL)BUTYRIC ACID(270596-51-5)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 270596-51-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Medicinal Chemistry:
BOC-(S)-3-AMINO-4-(3-FLUOROPHENYL)BUTYRIC ACID is used as a building block for the development of new pharmaceutical compounds due to its unique structure and the presence of a BOC protecting group, which facilitates its incorporation into complex molecules without unwanted side reactions.
Used in Peptide Synthesis:
In the field of peptide synthesis, BOC-(S)-3-AMINO-4-(3-FLUOROPHENYL)BUTYRIC ACID is used as a protected amino acid for the assembly of peptides. The BOC group allows chemists to add this compound to growing peptide chains without the risk of premature reaction at the amino group, ensuring the correct sequence and structure of the final peptide product.
Used in Research and Development:
BOC-(S)-3-AMINO-4-(3-FLUOROPHENYL)BUTYRIC ACID is utilized as a research tool in various scientific studies, particularly in the exploration of new synthetic routes, the investigation of the properties of chiral compounds, and the development of novel methodologies in organic and medicinal chemistry.
Used in Drug Design and Optimization:
BOC-(S)-3-AMINO-4-(3-FLUOROPHENYL)BUTYRIC ACID is employed as a starting material or intermediate in the design and optimization of drug candidates. Its unique structural features, including the fluorophenyl group and the chiral center, can contribute to the development of molecules with specific biological activities and selectivity.
Used in Chemical Synthesis:
BOC-(S)-3-AMINO-4-(3-FLUOROPHENYL)BUTYRIC ACID is used as a reactant in various chemical synthesis processes, where its functional groups can be further modified to produce a range of related compounds with potential applications in different industries.

InChI:InChI=1/C15H20FNO4/c1-15(2,3)21-14(20)17-12(9-13(18)19)8-10-5-4-6-11(16)7-10/h4-7,12H,8-9H2,1-3H3,(H,17,20)(H,18,19)/t12-/m0/s1

Upstream product

• 114873-11-9 boc-L-3-(3-fluorophenyl)alanine 

Relevant articles and documents

Synthesis method of chiral N-Boc-3-amino-4-aryl-butyric acid

The invention relates to a synthesis method of chiral N-Boc-3-amino-4-aryl-butyric acid. The method is as below: 1, conducting a cross metathesis reaction, an asymmetric conjugate addition reaction and an oxidation reaction on starting materials including an allyl aromatic compound and crotonaldehyde by a continuous reaction one-pot method to synthesize an N-Boc-3-aryl methyl-5-oxo isoxazole intermediate; or conducting an asymmetric conjugate addition reaction and an oxidation reaction on a starting material (E)-4-aryl-2-crotonaldehyde by a continuous reaction one-pot method to synthesize an N-Boc-3-aryl methyl-5-oxo isoxazole intermediate; and 2, subjecting (3R)-N-Boc-3-aryl methyl-5-oxo isoxazole intermediate by high-pressure hydrogenation to directly prepare the chiral N-Boc-3-amino-4-aryl-butyric acid. The synthesis method provided by the invention has the advantages of simple operation, mild reaction conditions, target product yield reaching 60-69%, and ee value of the target product reaching as high as 96%. The synthetic route has industrialization prospect.

Discovery of potent and selective β-homophenylalanine based dipeptidyl peptidase IV inhibitors

Modification of in-house screening lead β-aminoacyl proline 8 gave an equipotent thiazolidide 9. Extensive SAR studies on the phenyl ring of 9 led to the discovery of a novel series of potent and selective DP-IV inhibitors. Introduction of a fluorine at the 2-position proved to be crucial for the potency of this series. The 2,5-difluoro (22q) and 2,4,5-trifluoro (22t) analogues were potent inhibitors of DP-IV (IC50 = 270, 119 nM, respectively).