114873-01-7

Basic information

• Product Name: BOC-L-3-FLUOROPHENYLALANINE
• Synonyms: RARECHEM BK PT 0026;(S)-2-TERT-BUTOXYCARBONYLAMINO-3-(3-FLUORO-PHENYL)-PROPIONIC ACID;(S)-N-BOC-3-FLUOROPHENYLALANINE;N-TERT-BUTOXYCARBONYL-3-FLUOROPHENYL-L-ALANINE;N-ALPHA-TERT-BUTYLOXYCARBONYL-3-FLUORO-L-PHENYLALANINE;N-ALPHA-T-BUTYLOXYCARBONYL-L-3-FLUOROPHENYLALANINE;N-ALPHA-T-BUTOXYCARBONYL-3-FLUORO-L-PHENYLALANINE;L-3-FLUOROPHENYLALANINE, BOC PROTECTED
• CAS NO: 114873-01-7
• Molecular Formula: C₁₄H₁₈FNO₄
• Molecular Weight: 283.3
• Product Categories: Amino Acids;Phenylalanine analogs and other aromatic alpha amino acids;Peptide;a-amino
• Mol File: 114873-01-7.mol
• Article Data: 6

Chemical Properties

• Melting Point: 75-80 °C
• Boiling Point: 425 °C at 760 mmHg
• Flash Point: 210.8 °C
• Appearance: off-white crystalline powder
• Density: 1.1918 (estimate)
• Vapor Pressure: 5.57E-08mmHg at 25°C
• Refractive Index: 1.517
• Storage Temp.: Keep Cold
• Solubility: slightly sol. in Ethanol
• PKA: 3.82±0.10(Predicted)
• BRN: 5347375
• CAS DataBase Reference: BOC-L-3-FLUOROPHENYLALANINE(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-L-3-FLUOROPHENYLALANINE(114873-01-7)
• EPA Substance Registry System: BOC-L-3-FLUOROPHENYLALANINE(114873-01-7)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 114873-01-7(Hazardous Substances Data)

Usage

Chemical Properties

off-white crystalline powder

InChI:InChI=1/C14H18FNO4/c1-14(2,3)20-13(19)16-11(12(17)18)8-9-5-4-6-10(15)7-9/h4-7,11H,8H2,1-3H3,(H,16,19)(H,17,18)/t11-/m1/s1

Upstream product

• 1073-06-9 3-fluorobromobenzene 
• 768-35-4 3-fluorophenylboronic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 19883-77-3 L-3-fluorophenylalanine 
• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 

Downstream Products

• 7655-65-4 (S)-2-amino-3-(3-fluorophenyl)propanoic acid hydrochloride 
• 119744-84-2 tert-butyl (S)-(1-amino-3-(3-fluorophenyl)-1-oxopropan-2-yl)carbamate 
• 125218-23-7 (S)-2-[(S)-2-(2-{2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-acetylamino}-acetylamino)-3-(3-fluoro-phenyl)-propionylamino]-4-methyl-pentanoic acid; hydrochloride 
• 848444-61-1 (S)-[1-(3-fluorobenzyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester 
• 1039454-03-9 C₂₃H₁₉FN₄O₆ 
• 1039453-93-4 C₂₂H₁₈FN₃O₅ 
• 1039454-27-7 C₂₂H₂₂FN₃O₅ 

Relevant articles and documents

New reagent for the introduction of Boc protecting group to amines: Boc-OASUD

A new reagent, tert-butyl (2,4-dioxo-3-azaspiro [5,5] undecan-3-yl) carbonate (Boc-OASUD) for the preparation of N-Boc-amino acids is described. The Boc-OASUD reacts with amino acids and their esters at room temperature in the presence of a base and gives N-Boc-amino acids and their esters in good yields and purity. Introduction of the Boc group takes place without racemization. The Boc-OASUD, being a solid and more stable, is a better alternative to di-tert-butyl dicarbonate which is low melting and has to be dispensed in plastic containers than glass because of its poor stability.

Chirality-Driven Mode of Binding of α-Aminophosphonic Acid-Based Allosteric Inhibitors of the Human Farnesyl Pyrophosphate Synthase (hFPPS)

Thienopyrimidine-based allosteric inhibitors of the human farnesyl pyrophosphate synthase (hFPPS), characterized by a chiral α-aminophosphonic acid moiety, were synthesized as enantiomerically enriched pairs, and their binding mode was investigated by X-ray crystallography. A general consensus in the binding orientation of all (R)- and (S)-enantiomers was revealed. This finding is a prerequisite for establishing a reliable structure-activity relationship (SAR) model.

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.