684-07-1

Usage

Uses

3,3,3-Trifluorolactic acid is used as pharmaceutical intermediate.

Upstream product

• 359-44-4 (±)-3,3,3-trifluoro-2-hydroxypropanenitrile 
• 94726-00-8 ethyl 3,3,3-trifluoro-2-hydroxypropanoate 
• 13089-11-7 methyl 3,3,3-trifluoropyruvate 
• 67-63-0 isopropyl alcohol 
• 126266-75-9 3,3-dichloro-1,1,1-trifluoroacetone 

Downstream Products

• 93496-85-6 methyl d,l-2-hydroxy-3,3,3-trifluoropropionate 
• 94726-00-8 ethyl 3,3,3-trifluoro-2-hydroxypropanoate 
• 1225204-19-2 N-phenyl-3,3,3-trifluorolactyl amide 
• 125969-76-8 N-benzyl-3,3,3-trifluorolactyl amide 
• 1044590-64-8 N-[6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-2,2-dimethyl-3,4-dihydro-2H-pyrano[2,3-b]pyridine-4-yl]-3,3,3-trifluoro-2-hydroxypropanamide 
• 1044586-63-1 (S)-N-[(R)-7-[2-chloro-4-(1,2,4-oxadiazol-3-yl)phenyl]-6-(4-chlorophenyl)-2,2-dimethyl-3,4-dihydro-2H-pyrano[2,3-b]pyridin-4-yl]-3,3,3-trifluoro-2-hydroxypropanamide 
• 1044586-62-0 (R)-N-[(R)-7-[2-chloro-4-(1,2,4-oxadiazol-3-yl)phenyl]-6-(4-chlorophenyl)-2,2-dimethyl-3,4-dihydro-2H-pyrano[2,3-b]pyridin-4-yl]-3,3,3-trifluoro-2-hydroxypropanamide 
• 1044586-64-2 (S)-N-[(S)-7-[2-chloro-4-(1,2,4-oxadiazol-3-yl)phenyl]-6-(4-chlorophenyl)-2,2-dimethyl-3,4-dihydro-2H-pyrano[2,3-b]pyridin-4-yl]-3,3,3-trifluoro-2-hydroxypropanamide 
• 1044586-65-3 (R)-N-[(S)-7-[2-chloro-4-(1,2,4-oxadiazol-3-yl)phenyl]-6-(4-chlorophenyl)-2,2-dimethyl-3,4-dihydro-2H-pyrano[2,3-b]pyridin-4-yl]-3,3,3-trifluoro-2-hydroxypropanamide 

Relevant academic research and scientific papers

Tandem crystallization strategies for resolution of 3,3,3-trifluorolactic acid [CF3CH(OH)COOH] by chiral benzylamines

Resolution of rac-3,3,3-trifluorolactic acid by diastereomeric salt formation was reinvestigated. The use of (S)-1-phenylethylamine gives coprecipitation of two diastereomeric phases, 1 (S)-[NH3CH(CH3)Ph](S)-[CF3CH(OH)COO] and 2 (S)-[NH3CH(CH3)Ph](R)-[CF3CH(OH)COO]·H2O. Pure phase 1 may be obtained using molecular sieves as desiccants. Resolution by (S,S)-2-amino-1-phenylpropan-1,3-diol gives monoclinic (S,S)-[NH3CH(CH2OH)CHOHPh] (R)-[CF3CH(OH)-COO] 3 with minor (S)-3,3,3-trifluorolactate contamination, which is precluded in the recrystallized orthorhombic form 4. A new resolution using inexpensive phenylglycinol gives pure phase 5 (S)-[NH3CH(CH2OH)Ph] (S)-[CF3CH(OH)COO] in 76% yield, 94% ee in a single step, in preference to its (S)-(R) diastereomer 6. Overall efficient resolution for both enantiomers of the trifluorolactic acid (each ca. 70% yield, 99% ee) may be achieved by various two-step “tandem” crystallizations, involving direct addition of either water or a second base to the filtrate from the initial reaction.

Uncatalyzed Meerwein-Ponndorf-Verley reduction of trifluoromethyl carbonyl compounds by high-temperature secondary alcohols

Noncatalytic Meerwein-Ponndorf-Verley (MPV) reduction of hexafluoroacetone and methyl ester of trifluoropyruvic acid into hexafluoroisopropanol (HFIP) and trifluorolactic esters, respectively can be achieved by heating with secondary alcohols at 210-250 °C without any catalyst.

Self-disproportionation of enantiomers of isopropyl 3,3,3-(trifluoro)lactate via sublimation: Sublimation rates vs. enantiomeric composition

The presented results convincingly demonstrate that self-disproportionation of enantiomers via sublimation is substantially more complex phenomenon then was previously believed. We demonstrate that the racemic form of isopropyl 3,3,3-trifluoro-2-hydroxypr

Synthetic application of 3,3-dichloro-1, 1, 1-trifluoroacetone (DCTFA) and 3,3,3-trichloro-1, 1, 1-trifluoroacetone (TCTFA) for trifluorolactic acid derivatives

Synthetic application of 3,3-dichloro-1,1,1-trifluoroacetone (DCTFA) and 3,3,3-trichloro-1,1,1-trifluoroacetone (TCTFA) for industrially important trifluorolactic acid derivatives is described. Trifluorolactic acid was obtained by hydrolysis of DCTFA unde

Process for producing 3,3,3-trifluoro-2-hydroxypropionic acid or its derivative

The invention relates to a process for producing 3,3,3-trifluoro-2-hydroxypropionic acid. This process includes the step of (a) bringing a 1,1-dihalogeno-3,3,3-trifluoroacetone into contact with a basic aqueous solution. The obtained 3,3,3-trifluoro-2-hydroxypropionic acid may be reacted with a C1-C6 lower alcohol under an acidic condition, thereby producing a 3,3,3-trifluoro-2-hydroxypropionate. This propionate may be reacted with a hydride reducing agent (e.g., sodium borohydride), thereby producing 3,3,3-trifluoro-2-hydroxypropanol. These products (i.e., 3,3,3-trifluoro-2-hydroxypropionic acid and its derivatives) are important intermediates for medicines and liquid crystals.

Simple Access to (R)- and (S)-3,3,3-Trifluorolactic Acid and to (R)- and (S)-(Trifluoromethyl)oxirane

Ethyl trifluoropyruvate (from hexafluoropropylene oxide) is reduced by NaBH4 to rac-trifluorolactic acid which is resolved on a 100-g scale by salt formation with (R,R)- and (S,S)-2-amino-1-phenyl-1,3-propanediol (readily available intermediates of industrial chloroamphenicol synthesis).The enantiomerically pure trifluorolactic acids (>99percent ee by GC analysis on cyclodextrin columns) are converted into (R)- and (S)-(trifluoromethyl)oxirane in an overall yield of 73percent by the following steps: esterification, THP protection of the OH group, LAH reduction and mesylation to the 2-THP-protected mesylate of 3,3,3-trifluoro-1,2-propanediol, and one-pot deprotection (Dowex 50) and cyclization (NaOCH2CH2OH) in ethylene glycol.The enantiomeric purity of the oxirane (b.p. 39 deg C, isolated on a 10-g scale) was determined by GC to be >99percent.Possible synthetic targets are mentioned which should be accessible in enantiomerically pure form from the (trifluoromethyl)oxirane described here. Key Words: Resolution by crystallization of diastereomeric salts / Perfluoropropylene oxide / Trifluoropyruvate / Capillary GC determination of ratios of enantiomers / Cyclodextrine-derived GC columns / Determination of the sense of chirality by chemical correlation / pKs of 3,3,3-trifluoro-2-hydroxypropanoic and 4,4,4-trifluoro-3-hydroxybutanoic acid

Facile Synthesis of α-Trifluoromethylated Alcohols from Trifluoroacetaldehyde Ethyl Hemiacetal

Trifluoroacetaldehyde ethyl hemiacetal reacted with nucleophilic organosilanes such as cyanotrimethylsilane, allyltrimethylsilane, or enol trimethylsilyl ethers in the presence of Lewis acid to afford a series of α-trifluoromethylated alcohols in high yield. Key Words: trifluoroacetaldehyde ethyl hemiacetal; Lewis acid; trimethylsilylated nucleophiles; carbon-carbon bond formation; α-trifluoromethylated alcohol.