23809-57-6

Usage

Uses

Used in Pharmaceutical Industry:
5,5,5-Trifluoronorvaline is used as a building block in the synthesis of various pharmaceuticals for its potential in the development of novel peptide-based drugs. Its enhanced stability and bioavailability contribute to the creation of more effective and targeted therapeutic agents.
Used in Medicinal Chemistry Research:
5,5,5-Trifluoronorvaline is used as a molecular probe in the investigation of protein-protein interactions and cellular signaling pathways. Its unique properties allow researchers to gain insights into the mechanisms of action and potential applications of new drugs and therapeutics.

InChI:InChI=1/C5H8F3NO2/c6-5(7,8)2-1-3(9)4(10)11/h3H,1-2,9H2,(H,10,11)/t3-/m0/s1

Upstream product

• 23809-63-4 5-(3,3,3-trifluoropropyl)imidazolidine-2,4-dione 
• 96563-56-3 N-acetyl-5,5,5-trifluoronorvaline 
• 118311-19-6 5,5,5-Trifluoro-2-[(Z)-hydroxyimino]-pentanoic acid 
• 120097-66-7 diethyl α-(N-acetylamino)-α-(3,3,3-trifluoropropyl)malonate 
• 406-87-1 4,4,4-trifluorobutanal 
• 143-33-9 sodium cyanide 
• 118311-18-5 5,5,5-trifluoro-2-oxopentanoic acid 
• 118325-20-5 5,5,5-Trifluoro-2-oxo-pentanoic acid tert-butylamide 
• 1859-47-8 2-(benzylamino)-5,5,5-trifluoropentanoic acid 
• 453556-65-5 (S)-2-((tert-butoxycarbonyl)amino)-5,5,5-trifluoropentanoic acid 
• 1010423-89-8 N-benzyl-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-4,4,4-trifluorobut-2-yn-1-amine 
• 1010423-91-2 tert-butyl (R)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-4,4,4-trifluorobutylcarbamate 
• 1010423-93-4 tert-butyl (2S,3S)-6,6,6-trifluoro-1,2-dihydroxyhexan-3-ylcarbamate 
• 2365-80-2 2-amino-5,5,5-trifluoropentanoic acid 

Downstream Products

• 1859-47-8 2-(benzylamino)-5,5,5-trifluoropentanoic acid 
• 122565-28-0 (S)-2-amino-5,5,5-trifluoropentanoic acid 
• 122565-29-1 (2R)-2-amino-5,5,5-trifluoropentanoic acid 
• 1392848-78-0 C₁₁H₁₀Cl₂F₃NO₃S 
• 1146699-67-3 (R)-2-(4-chlorophenylsulfonamido)-5,5,5-trifluoropentanamide 
• 1392848-77-9 (R)-2-(4-chlorophenylsulfonamido)-5,5,5-trifluoropentanoic acid 
• 1582185-20-3 C₃₃H₃₃F₅N₄O₆ 
• 1582185-21-4 (2R,3R)-3-(((S)-6,6-difluoro-8-oxo-11-phenyl-6,7,8,9-tetrahydro-5H-4-oxa-7a,10-diazabenzo[ef]heptalen-9-yl)carbamoyl)-6,6,6-trifluoro-2-(3-methylisoxazol-4-yl)hexanoic acid 
• 1582184-06-2 (2R,3R)-N-((7S)-3,3-difluoro-6-oxo-9-phenyl-3,4,6,7-tetrahydro-2H-[1,4]diazepino[1,7,6-ef][1,5]benzoxazepin-7-yl)-3-(3-methyl-4-isoxazolyl)-2-(3,3,3-trifluoropropyl)succinamide 
• 1582184-67-5 (2R,3R)-1-benzyl 4-tert-butyl 3-(4-methylisoxazol-3-yl)-2-(3,3,3 trifluoropropyl)succinate 
• 1581734-82-8 (2R,3R)-1-benzyl 4-tert-butyl 3-phenyl-2-(3,3,3-trifluoropropyl)succinate 
• 1581734-81-7 benzyl (2R)-5,5,5-trifluoro-2-{[(trifluoromethyl)sulfonyl]oxy}pentanoate 
• 1581734-80-6 benzyl (2R)-5,5,5-trifluoro-2-hydroxypentanoate 
• 1581734-83-9 (R)-2-((R)-2-(tert-butoxy)-2-oxo-1-phenylethyl)-5,5,5-trifluoropentanoic acid 

Relevant academic research and scientific papers

MODULATORS OF SESTRIN-GATOR2 INTERACTION AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same.

MODULATORS OF SESTRIN-GATOR2 INTERACTION AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same.

Chemical deracemization and (S) to (R) interconversion of some fluorine-containing α-amino acids

Several ω-CF3-substituted a-amino acids have been prepared in optically pure form via two complementary approaches. Racemic fluorinated derivatives of 2-aminobutanoic acid, norvaline and norleucine were chemically deracemized by complexation with a Ni(II) salt and a chiral reagent derived from α-(phenyl)ethylamine. Additionally this procedure also allowed the conversion of readily available L-amino acids, CF3-analogs of cysteine and methionine, into the corresponding unnatural D-series. Optically pure amino acids are obtained upon disassembly of the Ni(II) complexes with recovery of the chiral ligand.

Enzymatic preparation of an R-amino acid intermediate for a γ-secretase inhibitor

(R)-5,5,5-Trifluoronorvaline, an intermediate for a γ-secretase inhibitor (BMS-708163) under development, was initially prepared from the corresponding keto acid using a commercially available d-amino acid dehydrogenase for reductive amination and glucose dehydrogenase for cofactor recycling. This amino acid could also be prepared using a d-amino acid transaminase with alanine as the amino donor, but the transamination also requires lactate dehydrogenase, NAD, formate, and formate dehydrogenase to remove pyruvate in order to bring the reaction to completion. An effective proprietary d-amino acid dehydrogenase was constructed by modification of the d-diaminopimelic acid dehydrogenase gene from Bacillus sphaericus, and a glucose dehydrogenase gene was cloned from Gluconobacter oxidans. Both genes were expressed in the same strain of Escherichia coli, and the glutamate dehydrogenase gene was inactivated in the expression strain to eliminate background production of the S-amino acid and improve the ee of the product to 100%. The amino acid could be isolated or converted without isolation to a p-chlorophenylsulfonamide carboxamide intermediate needed for the synthetic route to the γ-secretase inhibitor development candidate.

NOVEL ALPHA-(N-SULFONAMIDO)ACETAMIDE COMPOUNDS INCORPORATING DEUTERIUM AS INHIBITORS OF BETA AMYLOID PEPTIDE PRODUCTION

The present disclosure provides novel deuterated alpha-(N-sulfonamido)acetamide compounds, their pharmaceutical composition, processes thereof and a method for the treatment of Alzheimer's disease, head trauma, traumatic brain injury, and/or dementia pugilistica and/or other conditions associated with β-amyloid peptide.

Novel Alpha-(N-Sulfonamido)Acetamide Compound as an Inhibitor of Beta Amyloid Peptide Production

The present invention provides a novel alpha-(N-sulfonamido)acetamide compound, its pharmaceutical composition, processes thereof and a method for the treatment of Alzheimer's disease and other conditions associated with β-amyloid peptide.

Nucleophilic addition of 3,3,3-trifluoropropynyllithium to d-glyceraldimine: Concise synthesis of both enantiomers of 5,5,5-trifluoronorvaline

3,3,3-Trifluoropropynyllithium, in situ generated by treatment of 2-bromo-3,3,3-trifluoro-1-propene 1 with 2.0 equiv. of LDA at -78 °C, was trapped with d-glyceraldimine 2 to give trifluoromethylated propargylic amine 4 in 55% yield. Starting from the key

Fluoro- and trifluoroalkyl-containing heterocyclic sulfonamide inhibitors of beta amyloid production and derivatives thereof

Compounds of Formula (I), are provided where T is CHO, CON, or C(OH)R1R2; R1 and R2 are hydrogen, optionally substituted lower alkyl, CF3, optionally substituted alkenyl, or optionally substituted alkynyl; R3 is hydrogen or optionally substituted lower alkyl; R4 is (CF3)nalkyl, (CF3)n(substitutedalkyl), (CF3)nalkylphenyl, (CF3)nalkyl(substitutedphenyl), or (F)ncycloalkyl; n=1-3; R5 is hydrogen, halogen, CF3, diene fused to Y when Y═C, or substituted diene fused to Y when Y═C; W, Y and Z are C, CR6 or N where at least one of W, Y or Z are C; R6 is hydrogen, halogen, or optionally substituted lower alkyl; X is O, S, SO2, or NR7; R7 is hydrogen, optionally substituted lower alkyl, optionally substituted benzyl, or optionally substituted phenyl; and R8 is lower alkyl, CF3, or optionally substituted phenyl. Methods of preparing and using these compounds for inhibiting beta amyloid production and for treatment of Alzheimer's Disease and Down's syndrome are also described.

Analgesic peptides with a trifluoronorvaline modification

The present invention relates to analgesic enkephalin derivatives represented by the following formula: and the acid salts thereof, wherein Tyr is L-tyrosine, A1 or A2 is a glycine, and that which is not a glycine is an optically active trifluoro amino acid of the formula: STR1 wherein n is an integer from 1-3 and m is 1 or 2; A3 is L-Phenylalanine, or N-methyl-(L)-phenylalanine, and A4 is L-Methionine, L-Met-OH, L-Met-ol or L-Met-NH2.

New and Effective Routes to Fluoro Analogues of Aliphatic and Aromatic Amino Acids

New and efficient syntheses of 4,4,4-trifluorovaline (1), 5,5,5-trifluoronorvaline (2), 5,5,5-trifluoroleucine (5), 6,6,6-trifluoronorleucine (6), 4,5,6,7-tetrafluorotryptophan (25), and α-(trifluoromethyl)-β-alanine are studied.Trifluorovaline (1) and trifluoronorvaline (2) are synthesized through amidocarbonylation of 2-(trifluoromethyl)propanal (2-TFMPA) and 3-(trifluoromethyl)propanal (3-TFMPA), respectively, followed by hydrolysis.Trifluoroleucine (5) and trifluoronorleucine (6) are synthesized by using modified Erlenmeyer's azlactone method from 2-TFMPA and 3-TFMPA, respectively. (S)- and (R)-trifluoronorvalines and trifluoronorleucines with high enantiomeric purities (95-100percent ee) are obtained through enzymatic optical resolution of N-acetyltrifluoronorvaline (4) and N-acetyltrifluoronorleucine (17) with the use of a porcine kidney acylase I.Optically active trifluoronorleucine is also obtained via the asymmetric hydrogenation of (Z)-N-benzoyldehydrotrifluoroleucine ethyl ester (10a-Z) with a chiral rhodium catalyst, ClO4, followed by hydrolysis.Unexpectedly high diastereoselectivities (80-87percent ee) are observed in the hydrogenation of (Z)-N-benzoyldehydrotrifluoroleucine ethyl ester (11b) and (Z)-N-benzoyl-4-(pentafluorophenyl)dehydronorvaline (14-Z) over palladium/carbon. 4,5,6,7-Tetrafluorotryptophan (25) and 4,5,6,7-tetrahydrotryptamine (30) are synthesized from 3-formyl-4,5,6,7-tetrafluoroindole (22a) in 51percent (four steps) and 83percent (two steps) overall yields, respectively. 4,5,6,7-Tetrafluoroindoleacetic acid (28) is obtained from 1-acetyl-3-(acetoxymethyl)-4,5,6,7-tetrafluoroindole (23a) in four steps in 65percent overall yield.The 3-formyl- and 1-acetyl-3-(acetoxymethyl)tetrafluoroindoles (22a, 23a) are prepared through selenium dioxide oxidation of 1-acyl-3-methyl-4,5,6,7-tetrafluoroindole (21), which is obtained via the cyclization of a Schiff base of 2-(pentafluorophenyl)propanal (2-PFPPA), in good yields.