142995-31-1

Basic information

• Product Name: BOC-L-3-Trifluoromethylphe
• Synonyms: N-ALPHA-T-BUTOXYCARBONYL-3-TRIFLUOROMETHYL-L-PHENYLALANINE;RARECHEM BK PT 0134;(S)-2-TERT-BUTOXYCARBONYLAMINO-3-(3-TRIFLUOROMETHYL-PHENYL)-PROPIONIC ACID;tert-Butoxycarbonyl-L-3-trifluoromethylphenylalanine;BOC-L-3-TRIFLUOROMETHYLPHE;BOC-L-3-TRIFLUOROMETHYLPHENYLALANINE;BOC-3-(TRIFLUOROMETHYL)-L-PHENYLALANINE;BOC-PHE(3-CF3)-OH
• CAS NO: 142995-31-1
• Molecular Formula: C₁₅H₁₈F₃NO₄
• Molecular Weight: 333.3
• Product Categories: Amino Acids;Phenylalanine analogs and other aromatic alpha amino acids;a-amino
• Mol File: 142995-31-1.mol
• Article Data: 1

Chemical Properties

• Melting Point: 135-138 °C
• Boiling Point: 423.2 °C at 760 mmHg
• Flash Point: 209.7 °C
• Appearance: /Solid
• Density: 1.271 g/cm³
• Vapor Pressure: 6.44E-08mmHg at 25°C
• Refractive Index: 1.487
• Storage Temp.: Keep Cold
• PKA: 3.79±0.10(Predicted)
• BRN: 7048145
• CAS DataBase Reference: BOC-L-3-Trifluoromethylphe(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-L-3-Trifluoromethylphe(142995-31-1)
• EPA Substance Registry System: BOC-L-3-Trifluoromethylphe(142995-31-1)

Safety Data

• Hazard Codes: Xi
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 142995-31-1(Hazardous Substances Data)

Usage

General Description

BOC-L-3-Trifluoromethylphe, also known as N-tert-butoxycarbonyl-3-trifluoromethyl-L-phenylalanine, is a synthetic chemical compound used in pharmaceutical research and development. It is a derivative of the amino acid phenylalanine and contains a trifluoromethyl group, which imparts distinct chemical and biological properties. BOC-L-3-Trifluoromethylphe has been studied for its potential pharmacological applications, including as a building block for the synthesis of peptide-based drugs and as a tool in the development of new medicinal compounds. Its unique chemical structure and reactivity make it a valuable tool in drug discovery and development processes.

InChI:InChI=1/C15H18F3NO4/c1-14(2,3)23-13(22)19-11(12(20)21)8-9-5-4-6-10(7-9)15(16,17)18/h4-7,11H,8H2,1-3H3,(H,19,22)(H,20,21)/t11-/m0/s1

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 14464-67-6 (2S)-2-amino-3-[3-(trifluoromethyl)phenyl]propanoic acid 

Downstream Products

• 944470-70-6 1,1-dimethylethyl ((1S)-2-hydroxy-1-{[3-(trifluoromethyl)phenyl]methyl}ethyl)carbamate 
• 938462-26-1 (2S)-2-amino-3-[3-(trifluoromethyl)phenyl]propan-1-ol 
• 1426343-20-5 C₃₂H₄₃F₃N₈O₅ 
• 1433950-22-1 C₂₁H₂₆F₃N₅O₄ 
• 1433856-92-8 C₁₆H₁₉F₃N₂O₃*ClH 
• 1426343-11-4 C₃₂H₄₃F₃N₈O₅ 
• 1240612-98-9 methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(3-(trifluoromethyl)phenyl)propanoate 
• 1104070-37-2 tert-butyl (S)-1-(5-(4-chlorothieno[2,3-c]pyridin-2-yl)-1,3,4-thiadiazol-2-ylamino)-1-oxo-3-(3-(trifluoromethyl)phenyl)propan-2-ylcarbamate 
• 1011726-65-0 C₃₂H₃₅F₃N₂O₅S 
• 142995-46-8 (2S,4R)-2-[(S)-1-(Benzyl-methyl-carbamoyl)-2-(3-trifluoromethyl-phenyl)-ethylcarbamoyl]-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester 

Relevant articles and documents

Studies of Neurokinin Antagonists. 4. Synthesis and Structure-Activity Relationships of Novel Dipeptide Substance P Antagonists: N2--L-prolyl>-N-methyl-N-(phenylmethyl)-3-(2-naphthyl)-L-alaninamide and Its Related Compounds

As an extension of our studies on discovering a novel substance P (SP) antagonist, we modified the previously reported dipeptide, N2-2-(1H-indol-3-ylcarbonyl)-L-lysyl>-N-methyl-N-(phenylmethyl)-L-phenylalaninamide (2b).The lysine part in 2b was first optimized to a (2S,4R)-hydroxyproline derivative (3h), which is 2-fold more potent than 2b in SP binding assay using guinea pig lung membranes.Next we modified the 1H-indol-3-ylcarbonyl part in 3h.Introduction of a methyl group at the indole nitrogen enhanced the oral activity, while retaining the binding activity.Finally, we modified the phenylalanine part to culminate in the most potent compound 7k (FK888), which is a potent SP antagonist with NK1 selectivity as well as oral activity.