269396-77-2

Basic information

• Product Name: BOC-(R)-3-AMINO-4-(2-TRIFLUOROMETHYL-PHENYL)-BUTYRIC ACID
• Synonyms: BOC-(R)-3-AMINO-4-(2-TRIFLUOROMETHYL-PHENYL)-BUTYRIC ACID;RARECHEM AK PT B028;N-T-BUTOXYCARBONYL-(R)-3-AMINO-4-(2-TRIFLUOROMETHYLPHENYL)BUTANOIC ACID;N-BETA-T-BUTOXYCARBONYL-D-HOMO(2-TRIFLUOROMETHYLPHENYL)ALANINE;(R)-3-(Boc-amino)-4-(2-trifluoromethylphenyl)butyric acid;Boc-D-b-HoPhe(2-CF3)-OH;Boc-D-β-HoPhe(2-CF3)-OH;(betaR)-beta-[[(tert-Butoxy)carbonyl]amino]-2-(trifluoromethyl)benzenebutanoic acid
• CAS NO: 269396-77-2
• Molecular Formula: C₁₆H₂₀F₃NO₄
• Molecular Weight: 347.33
• Product Categories: 3-Amino-4-phenylbutanoic Acid Analogs;B-Amino
• Mol File: 269396-77-2.mol

Chemical Properties

• Boiling Point: 440.474 °C at 760 mmHg
• Flash Point: 220.191 °C
• Appearance: /
• Density: 1.246
• Vapor Pressure: 1.55E-08mmHg at 25°C
• Refractive Index: 1.486
• PKA: 4.39±0.10(Predicted)
• CAS DataBase Reference: BOC-(R)-3-AMINO-4-(2-TRIFLUOROMETHYL-PHENYL)-BUTYRIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-(R)-3-AMINO-4-(2-TRIFLUOROMETHYL-PHENYL)-BUTYRIC ACID(269396-77-2)
• EPA Substance Registry System: BOC-(R)-3-AMINO-4-(2-TRIFLUOROMETHYL-PHENYL)-BUTYRIC ACID(269396-77-2)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 269396-77-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Development:
Boc-(R)-3-Amino-4-(2-trifluoromethyl-phenyl)-butyric acid is used as a building block in the synthesis of peptide drugs for its potential applications in the treatment of various medical conditions. Its specific structure, including the Boc-protecting group and the trifluoromethyl-phenyl functional group, makes it valuable for creating novel drug candidates with improved properties and bioavailability.
Used in Drug Discovery:
In the field of drug discovery, Boc-(R)-3-Amino-4-(2-trifluoromethyl-phenyl)-butyric acid is utilized for its chirality and unique pharmacological activity due to its (R)-configuration. This feature allows researchers to explore its potential in developing new therapeutic agents with enhanced efficacy and selectivity.
Used in Medicinal Chemistry:
Boc-(R)-3-Amino-4-(2-trifluoromethyl-phenyl)-butyric acid is employed in medicinal chemistry as a key component in the design and synthesis of new pharmaceutical compounds. Its unique structural features enable the development of drugs with targeted actions and reduced side effects, contributing to the advancement of personalized medicine.
Used in Drug Synthesis:
In the synthesis of drugs, Boc-(R)-3-Amino-4-(2-trifluoromethyl-phenyl)-butyric acid serves as an essential intermediate, facilitating the creation of complex molecular structures with specific therapeutic properties. Its presence in the synthesis process can lead to the development of innovative medications with improved pharmacokinetics and pharmacodynamics.
Overall, Boc-(R)-3-Amino-4-(2-trifluoromethyl-phenyl)-butyric acid is a versatile and important chemical compound in the pharmaceutical industry, with applications spanning from drug discovery and development to medicinal chemistry and drug synthesis. Its unique structural features and chirality make it a promising candidate for the creation of novel and effective therapeutic agents.

InChI:InChI=1/C16H20F3NO4/c1-15(2,3)24-14(23)20-11(9-13(21)22)8-10-6-4-5-7-12(10)16(17,18)19/h4-7,11H,8-9H2,1-3H3,(H,20,23)(H,21,22)/t11-/m1/s1

Relevant articles and documents

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).