1213132-66-1

Basic information

• Product Name: METHYL (2R)-2-AMINO-3-(2,4,5-TRIFLUOROPHENYL)PROPANOATE
• Synonyms: D-Phenylalanine, 2,4,5-trifluoro-, methyl ester;methyl 2-amino-3-(2,4,5-trifluorophenyl)propanoate;METHYL (2R)-2-AMINO-3-(2,4,5-TRIFLUOROPHENYL)PROPANOATE
• CAS NO: 1213132-66-1
• Molecular Formula: C₁₀H₁₀F₃NO₂
• Molecular Weight: 233.19
• Mol File: 1213132-66-1.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: METHYL (2R)-2-AMINO-3-(2,4,5-TRIFLUOROPHENYL)PROPANOATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL (2R)-2-AMINO-3-(2,4,5-TRIFLUOROPHENYL)PROPANOATE(1213132-66-1)
• EPA Substance Registry System: METHYL (2R)-2-AMINO-3-(2,4,5-TRIFLUOROPHENYL)PROPANOATE(1213132-66-1)

Safety Data

• Hazardous Substances Data: 1213132-66-1(Hazardous Substances Data)

Usage

General Description

Methyl (R)-2-amino-3-(2,4,5-trifluorophenyl)propanoate is a chemical compound with the molecular formula C11H12F3NO2. It is an amino acid derivative and is commonly used in pharmaceutical research and drug development. methyl (R)-2-amino-3-(2,4,5-trifluorophenyl)propanoate has a chiral center and exists as a pair of enantiomers, with the (R)-enantiomer being the biologically active form. The presence of the trifluorophenyl group in the molecule makes it a useful tool for studying drug-receptor interactions and for designing new pharmaceutical compounds. It has potential applications in the treatment of various medical conditions but also requires careful handling and study due to its complex structure and potential biological activity.

Upstream product

• 165047-24-5 2,4,5-trifluorobenzaldehyde 
• 486460-07-5 (2S,5R)-2,5-dihydro-3,6-dimethoxy-2-isopropyl-5-(2',4',5'-trifluorobenzyl)-pyrazine 

Downstream Products

• 486460-08-6 (R)-methyl 2-((tert-butoxycarbonyl)amino)-3-(2,4,5-trifluorophenyl)propanoate 

Relevant articles and documents

Biocatalytic retrosynthesis approaches to d-(2,4,5-trifluorophenyl)alanine, key precursor of the antidiabetic sitagliptin

The integration of biocatalytic steps in retrosynthetic analysis of a target molecule offers multiple advantages, such as reduction of the environmental footprint of the process, viability of milder and safer reaction conditions, and accessibility of transformations that are challenging with traditional chemical synthesis. Herein, six chemo-enzymatic routes are described for the synthesis of a fluorinated d-phenylalanine derivative, precursor of the blockbuster antidiabetic drug sitagliptin. All routes start from the same aldehyde precursor and involve at least one biocatalytic step, including reductive amination, transamination, deracemisation, hydroamination, and alkene reduction. The target molecule was obtained in 2-5 steps from the aldehyde, with ee up to >99% and in 36-62% isolated yield. Furthermore, as part of one of the routes, the first example of a fully biocatalytic conversion of a cinnamic acid derivative to the corresponding d-phenylalanine (formal d-selective hydroamination) is reported.

3-AMINO-4-PHENYLBUTANOIC ACID DERIVATIVES AS DIPEPTIDYL PEPTIDASE INHIBITORS FOR THE TREATMENT OR PREVENTION OF DIABETES

The present invention is directed to 3-amino-4-phenylbutanoic acid derivatives which are inhibitors of the dipeptidyl peptidase-IV enzyme ("DP-IV inhibitors") and which are useful in the treatment or prevention of diseases in which the dipeptidyl peptidase-IV enzyme is involved, such as diabetes and particularly type 2 diabetes. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which the dipeptidyl peptidase-IV enzyme is involved.