218608-97-0

Basic information

• Product Name: BOC-(S)-3-AMINO-4-(4-FLUORO-PHENYL)-BUTYRIC ACID
• Synonyms: BOC-4-FLUORO-L-BETA-HOMOPHENYLALANINE;BOC-BETA-HOPHE(4-F)-OH;BOC-(S)-3-AMINO-4-(4-FLUOROPHENYL)BUTANOIC ACID;BOC-(S)-3-AMINO-4-(4-FLUORO-PHENYL)-BUTYRIC ACID;BOC-PHE(4-F)-(C*CH2)OH;N-T-BUTOXYCARBONYL-(S)-3-AMINO-4-(4-FLUOROPHENYL)BUTANOIC ACID;N-BETA-T-BUTOXYCARBONYL-L-HOMO(4-FLUOROPHENYL)ALANINE;RARECHEM AK PT B065
• CAS NO: 218608-97-0
• Molecular Formula: C15H20FNO4
• Molecular Weight: 297.32
• Product Categories: 3-Amino-4-phenylbutanoic Acid Analogs;pharmacetical;B-Amino
• Mol File: 218608-97-0.mol

Chemical Properties

• Melting Point: 130-132°C
• Boiling Point: 449.3 °C at 760 mmHg
• Flash Point: 225.5 °C
• Appearance: /
• Density: 1.192 g/cm³
• Vapor Pressure: 7.4E-09mmHg at 25°C
• Refractive Index: 1.514
• Storage Temp.: 2-8°C
• PKA: 4.42±0.10(Predicted)
• CAS DataBase Reference: BOC-(S)-3-AMINO-4-(4-FLUORO-PHENYL)-BUTYRIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-(S)-3-AMINO-4-(4-FLUORO-PHENYL)-BUTYRIC ACID(218608-97-0)
• EPA Substance Registry System: BOC-(S)-3-AMINO-4-(4-FLUORO-PHENYL)-BUTYRIC ACID(218608-97-0)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• HazardClass: IRRITANT
• Hazardous Substances Data: 218608-97-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
BOC-(S)-3-AMINO-4-(4-FLUORO-PHENYL)-BUTYRIC ACID is used as a building block for the synthesis of peptide-based drugs due to its potential to contribute to the development of novel therapeutic agents.
Used in Medicinal Chemistry Research:
BOC-(S)-3-AMINO-4-(4-FLUORO-PHENYL)-BUTYRIC ACID is used as a research tool for studying the effects of fluorine substitution on the pharmacological properties of compounds, which can be instrumental in the design of new drugs with improved efficacy and selectivity.
Used in Neurobiology Research:
BOC-(S)-3-AMINO-4-(4-FLUORO-PHENYL)-BUTYRIC ACID is utilized in the study of neurobiology and neurotransmitter systems, potentially aiding in the understanding of the roles and interactions of amino acid derivatives in the nervous system.

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

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).