44864-47-3

Usage

Uses

Used in Pharmaceutical Industry:
(R)-3,3,3-TRIFLUORO-2-HYDROXY-2-METHYLPROPIONIC ACID is used as a chiral building block for the development of new drugs with improved efficacy and selectivity. Its unique stereochemistry allows for the creation of enantiomerically pure compounds, which can exhibit different biological activities and reduce potential side effects.
Used in Chemical Synthesis:
(R)-3,3,3-TRIFLUORO-2-HYDROXY-2-METHYLPROPIONIC ACID is used as a key intermediate in the synthesis of various specialty chemicals, including agrochemicals, fragrances, and other fine chemicals. Its versatile functional groups enable a wide range of chemical reactions, leading to the formation of diverse products with specific applications.
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InChI:InChI=1/C4H5F3O3/c1-3(10,2(8)9)4(5,6)7/h10H,1H3,(H,8,9)/t3-/m1/s1

Upstream product

• 374-35-6 3,3,3-trifluoro-2-hydroxy-2-methylpropionic acid 
• 337-16-6 2-hydroxy-2-methyl-3,3,3-trifluoropropionic acid methyl ester 
• 693287-30-8 (R)-2,3-epoxy-2-(trifluoromethyl)propionic acid 
• 114645-34-0 (R,S)-3,3,3-trifluoro-2-hydroxy-2-methylpropionamide 

Downstream Products

• 243982-42-5 N-cyclohexyl-3,3,3-trifluoro-2-hydroxy-2-methyl-propionamide 
• 243982-46-9 (R)-N-(2-Chlorophenyl)-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide 
• 242139-87-3 (R)-N-[2-chloro-4-iodophenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide 
• 329926-82-1 (R)-N-(2-methyl-3-fluoro-4-iodophenyl)-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide 
• 329794-58-3 (R)-[5-(4-methylsulphanylphenylsulphanyl)-1-(3,3,3-trifluoro-2-hydroxy-2-methylpropionyl)indoline] 
• 1310351-08-6 {(R)-5,5-difluoro-4-[2-fluoro-5-((R)-3,3,3-trifluoro-2-hydroxy-2-methyl-propionylamino)-phenyl]-4-methyl-5,6-dihydro-4H-[1,3]oxazin-2-yl}-carbamic acid tert-butyl ester 
• 1360607-89-1 4-((3-chloro-4-(3,3,3-trifluoro-2-hydroxy-2-methylpropanamido)phenyl)thio)N,N-dimethylbenzamide 
• 329925-77-1 (2R)-N-[2-chloro-4-(ethylsulfonyl)-3-fluorophenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide 

Relevant academic research and scientific papers

Efficient preparation of both enantiomers of 3,3,3-trifluoro-2-hydroxy-2- methylpropanoic acid catalyzed by Shinella sp. R-6 and Arthrobacter sp. S-2

Several microorganisms that can enantioselectively hydrolyze 3,3,3-trifluoro-2-hydroxy-2-methylpropanamide have been isolated from soil samples. These strains were capable of growing in a medium containing 3,3,3-trifluoro-2-hydroxy-2-methylpropanamide as the sole nitrogen source. Among them, Shinella sp. R-6 was identified as a strain capable of exhibiting R-selective hydrolysis activity, while Arthrobacter sp. S-2 was capable of exhibiting S-selective hydrolysis activity. The preparation of both enantiomers of 3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acid via the two-step whole-cell reaction was investigated using these two strains.

Optically active fluorine-containing compounds and processes for their production

An optically active fluorine-containing compound represented by the following formula (1) or (2) wherein A is an oxygen atom, a sulfur atom or an NH group, and R1 selected from a variety of organic group, is used in the preparation of (S)- or (R)-3,3,3-trifluoro-2-hydroxy-2-methylpropionic acid.

Substituted N-phenyl 2-hydroxy-2-methyl-3,3,3-trifluoropropanamide derivatives which elevate pyruvate dehydrogenase activity

A compound of formula (I) wherein: n is 1 or 2; R 1 is chloro, fluoro, bromo, methyl or methoxy; R 2 is as defined within; R 3 is as defined within; and R 4 is hydrogen or fluoro; or a pharmaceutically acceptable salt or an in vivo hydrolysable ester thereof is described. The use of compounds of formula (I) in the production of an elevation of PDH activity in a warm-blooded animal such as a human being are also described. Pharmaceutical compositions, methods and processes for preparation of compounds of formula (I) are detailed. STR1

Benzenesulfonamide-derivatives and their use as medicaments

Compounds of formula (I), pharmaceutically acceptable salts or in vivo hydrolysable esters thereof, wherein: Ring X is phenyl or a six membered heteroaryl ring containing one or two ring nitrogens where said nitrogens are optionally oxidised to form the N

Selection, purification, characterisation, and cloning of a novel heat-stable stereo-specific amidase from Klebsiella oxytoca, and its application in the synthesis of enantiomerically pure (R)- and (S)-3,3,3-trifluoro-2-hydroxy-2-methylpropionic acids and (S)-3,3,3-trifluoro-2-hydroxy-2-methylpropionamide

We isolated, characterised, and cloned an enantio-specific amidase from Klebsiella oxytoca and used it to resolve (R,S)-3,3,3-trifluoro-2-hydroxy-2-methylpropionamide, giving (R)3,3,3-trifluoro-2-hydroxy-2-methylpropionic acid and (S)-3,3,3-trifluoro-2-hydroxy-2-methylpropionamide. The (S)-amide could then be hydrolysed chemically to (S)-3,3,3-trifluoro-2-hydroxy-2-methylpropionic acid. The process can therefore be adapted to produce both (R)-and (S)-enantiomers of 3,3,3-trifluoro-2-hydroxy-2-methylpropionic acid, or (S)-3,3,3-trifluoro-2-hydroxy-2-methylpropionamide. The biocatalytic step is part of a combined chemical and biocatalytic route that starts from ethyl trifluoroacetoacetate. The products typically have a purity of greater than 98% and ee values of essentially 100% after isolation. The process has been used to produce 100-g amounts of the (S)-acid, and successfully scaled up to produce 100-kg amounts of the (R)-acid, with the biotransformation carried out at the 1500-L scale.

Process for producing optically active 3,3,3-Trifluoro-2-Hydroxy-2-Methylpropionic acid, and salt thereof

There are disclosed are a diastereomer salt of formula (1): a process for producing the same, a process for producing optically active 3,3,3-trifluoro-2-hydroxy-2-methylpropionic acid of formula (2′): a novel optically active amine compound of formula (4): a novel optically active amine compound of formula (8): an imine compound of formula (7) or (11):

Use of compounds for the elevation of pyruvate dehydrogenase activity

The use of compounds of the formula (I), and salts thereof; and pharmaceutically acceptable in vivo cleavable prodrugs of said compound of formula (I); and pharmaceutically acceptable salts of said compound or said prodrugs: wherein: Ring C is phenyl or a carbon linked heteroaryl ring substituted as defmed within; R1is an ortho substituent as defined within; n is 1 or 2; A—B is a linking group as defined within; R2and R3are as defined within; R4is hydroxy, hydrogen, halo, amino or methyl; in the manufacture of a medicament for use in the elevation of PDH activity in warm-blooded animals such as humans is described. Pharmaceutical compositions, methods and processes for preparation of compounds of formula (I) are also described.

Tricyclic compounds

The present invention provides tricyclic compounds which are useful for the treatment of pollakiuria and urinary incontinence and which are represented by general formula (I): (whereinR1 represents hydrogen, substituted or unsubstituted lower a

The synthesis of (R)- and (S)-α-trifluoromethyl-α-hydroxycarboxylic acids via enzymatic resolutions

Kinetic resolution of 1, 1, 1-trifluoro-2-alkanone cyanohydrin acyl derivatives with Candida rugosa lipase afforded the remaining (R)-enantiomer in high selectivity (E from 30 to >200). Candida rugosa lipases from several suppliers were compared and found

Tricyclic compounds

The present invention relates to tricyclic compounds represented by general formula (I) which are useful as therapeutic agents for urinary incontinence: STR1 wherein R1 represents hydrogen and the like; --X1 --X2 --X3