1578-62-7

Usage

Uses

Used in Pharmaceutical Research:
2-Fluoro-3-methylbutyric acid is utilized as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique fluoro-substitution can impart distinct properties to the molecules it is incorporated into, potentially enhancing their efficacy, selectivity, or metabolic stability.
Used in Drug Development:
In the pharmaceutical industry, 2-Fluoro-3-methylbutyric acid is employed as a building block for the development of new drugs. Its incorporation into drug candidates can lead to improved pharmacokinetic and pharmacodynamic profiles, which are crucial for the success of a drug in clinical trials and eventual market approval.

InChI:InChI=1/C5H9FO2/c1-3(2)4(6)5(7)8/h3-4H,1-2H3,(H,7,8)

Upstream product

• 1775-47-9 2-Fluor-2-isopropyl-malonsaeure-diethylester 
• 18283-04-0 2-Ethoxycarbonimidoyl-2-fluoro-3-methyl-butyric acid ethyl ester 
• 516-06-3 D,L-valine 
• 135359-27-2 2-Fluoro-3-methyl-butyric acid methyl ester 
• 17417-00-4 methyl 2-hydroxy-3-methylbutanoate 
• 72-18-4 L-valine 
• 108-12-3 isopentanoyl chloride 
• 1116395-31-3 (S)-2-fluoro-3-methyl-butyric acid R-(+)-α-methylbenzylamine salt 
• 3213-49-8 ethyl 2-isopropylcyanoacetate 
• 146746-20-5 (S)-(-)-methyl 2-methanesulfonyloxy-3-methylbutanoate 
• 145589-03-3 (S)-4-benzyl-3-(3-methylbutanoyl)oxazolidin-2-one 
• 669074-37-7 (S)-4-Benzyl-3-((S)-2-fluoro-3-methyl-butyryl)-oxazolidin-2-one 

Downstream Products

• 1190832-63-3 C₁₁H₁₅FN₂O 
• 669074-38-8 (S)-2-((S)-2-Fluoro-3-methyl-butyrylamino)-propionic acid tert-butyl ester 
• 143238-68-0 2'-<6'-((2''S-2''-fluoro-3''-methylbutanoyl)oxy)>naphthyl 4-decyloxybenzoate 
• 669074-39-9 (S)-2-((S)-2-Fluoro-3-methyl-butyrylamino)-propionic acid 

Relevant academic research and scientific papers

Studies of a diastereoselective electrophilic fluorination reaction employing a cryo-flow reactor

The application of meso-scale flow chemistry in research laboratories continues to increase. Here, we report on the use of a modular cryo-flow device as applied to a diastereoselective fluorination process. The reactor can be incorporated into existing flow chemistry setups to permit continuous processing at low temperatures without recourse to cryogenic consumables. Georg Thieme Verlag Stuttgart. New York.

Conformational preference in bis(porphyrin) tweezer complexes: A versatile chirality sensor for α-chiral carboxylic acids

Metallated porphyrin tweezers have demonstrated a remarkable ability to function as reporters of absolute stereochemistry for a number of different classes of organic molecules. Flexibility in binding, however, can result in an ensemble of different Exciton Coupled Circular Dichroism (ECCD) active conformations that could lead to variable results. Linker flexibility was found to be a key determinant of binding conformation. Experimental results indicate that a balance between linker flexibility and rigidity could yield an optimum porphyrin tweezer that stabilizes a common conformation for all bound chiral guests. This leads to a more simplified approach to absolute stereochemical determination of asymmetry for small organic molecules. This was demonstrated by the use of a C3-linked zincated porphyrin tweezer that yields a common conformational preference for a variety of α-chiral carboxylic acids derivatized with a diamine carrier. Copyright

AZEPINE DERIVATIVES AS GAMMA-SECRETASE INHIBITORS

Compounds of formula (I), pharmaceutical compositions comprising them, and methods for their use are described.

An unusual conformation of α-haloamides due to cooperative binding with zincated porphyrins

CD and NMR spectroscopic evidence of cooperative binding between an α-halogen atom and a carboxamide group with a zinc porphyrin leads to an unprecedented conformation for the determination of the absolute stereochemistry of α-haloamides (α-halocarboxylic acids derivatized with 1,4-phenylenediamine) through the use of exciton-coupled circular dichroism (ECCD). With the use of chiral lactams, whose rotomeric contributions are minimized, both ECCD and NMR spectroscopy demonstrate that the porphyrin favors binding to the side of the sterically more demanding halogen atom as compared to the smaller hydrogen atom. In all, the data is strongly suggestive of an unusual conformation not observed before for α-chiral amides. A mnemonic for determining the absolute stereochemistry of α-halogenated carboxylic acids is provided.

P3 cap modified Phe*-Ala series BACE inhibitors

With the aim of reducing molecular weight and adjusting log D value of BACE inhibitors to more favorable range for BBB penetration and better bioavailability, we synthesized and evaluated several series of P3 cap modified BACE inhibitors obtained via replacement of the P3 NHBoc moiety as seen in 3 with other polar functional groups such as amino, hydroxyl and fluorine. Several promising inhibitors emerging from this P3 cap SAR study (e.g., 15 and 19) demonstrated good enzyme inhibitory potencies (BACE-1 IC50 50 ～1 μM).

Simple synthesis of optically active 2-fluoropropanoic acid and analogs of high enantiomeric purity

A very simple synthesis of optically active 2-fluoropropanoic acid 1 (R=CH3, R′=H) and analogs of high enantiomeric purity was developed using the sulfonates 2 of the corresponding optically active 2-hydroxycarboxylic esters and potassium fluor

Synthesis and study of new α-haloacid ferroelectric liquid crystal derivatives. MM2 approach to the molecular structure-ferroelectric activity relationship

In order to understand the structural factors that influence ferroelectric properties, three new series (F, Cl, and Br) of chiral naphthalene-ring derived compounds were synthesized, and their ferroelectric properties [spontaneous polarization (Ps) and response time (τ)] were evaluated in the pure compound. The chiral tails are α-halo acids derived from L-α-amino acids: L-α-alanine (1), L-leucine (2), L-isoleucine (3), and L-valine (4), with a fluorine, chlorine, or bromine atom in the chiral center. The highest Ps values were obtained for compounds containing a fluorine or chlorine atom in their asymmetric center and with chiral tail derived from L-isoleucine (3) (F-3, 102 nC/cm2; Cl-3, 100 nC/cm2). The steric requirements of the halogen atom and the bulky alkyl group in the asymmetric center determine the most stable conformations of these chiral tails, which have been studied by molecular mechanic empirical calculations, MM2. MM2 calculations prove to be a successful tool for understanding how the structure of the lateral chiral tail affects molecular arrangement and, as a consequence, the ferroelectric properties of the materials.

Synthesis and Ferroelectric Properties of 2,5-Diphenylpyrimidines with Different α-Fluorocarboxylic Acids

Chiral esters of 2--5-pyrimidine and 2--5-pyrimidine with four different α-fluorocarboxylic acids have been synthesized.The spontaneous polarization and the tilt angles in the smectic C* phase were measured as a function of temperature.All compounds exhibit wide range smectic C* phases, the highest values of the spontaneous polarization being about 400 nC/cm2.Additionally the spontaneous polarization in a higher ordered smectic phase was determined, the values ranging up to about 600 nC/cm2.The spontaneous polarization/tilt angle ratio strongly increases with decreasing temperature. - Keywords: Liquid Crystals, Smectic Liquid Crystals, Ferroelectric Properties, Chiral α-Fluorocarboxylic Acid Esters, 2,5-Diphenylpyrimidines

THE TRANSFORMATION OF α-AMINOACIDS INTO FLUOROACIDS

The reactions of some α-aminoacids with excess sodium nitrite in polyhydrogen fluoride-pyridine are described.

Synthetic Methods and Reactions. Part 106. Suppression of Anchimerically Assisted Rearrangement Products in the Synthesis of α-Fluorocarboxylic Acids from α-Amino Acids with 48:52 (w/w) Hydrogen Fluoride/Pyridine

Anchimerically assisted rearrangement, observed in the fluorination of some α-amino acids with 70:30 (w/w) hydrogen fluoride/pyridine (by weight) in the presence of NaNO2, is substantially or fully suppressed by using the less acidic reagent 48:52 (w/w) hydrogen fluoride/pyridine.