137496-70-9

Basic information

• Product Name: 1-Pyrrolidinecarboxylic acid, 2-[[(3,5-dimethylphenyl)amino]carbonyl]-, 1,1-dimethylethyl ester, (S)-
• Synonyms: (S)-2-(3,5-Dimethyl-phenylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
• CAS NO: 137496-70-9
• Molecular Formula: C18H26N2O3
• Molecular Weight: 318.416
• Mol File: 137496-70-9.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: 1-Pyrrolidinecarboxylic acid, 2-[[(3,5-dimethylphenyl)amino]carbonyl]-, 1,1-dimethylethyl ester, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Pyrrolidinecarboxylic acid, 2-[[(3,5-dimethylphenyl)amino]carbonyl]-, 1,1-dimethylethyl ester, (S)-(137496-70-9)
• EPA Substance Registry System: 1-Pyrrolidinecarboxylic acid, 2-[[(3,5-dimethylphenyl)amino]carbonyl]-, 1,1-dimethylethyl ester, (S)-(137496-70-9)

Safety Data

• Hazardous Substances Data: 137496-70-9(Hazardous Substances Data)

Usage

Purpose

Antidiabetic medication

Mechanism of action

Inhibits the enzyme DPP-4 (dipeptidyl peptidase-4)

Effect on blood sugar levels

Increases insulin levels and decreases glucagon levels

Administration

Orally

Approved for use

Treatment of type 2 diabetes

Precautions

Consult with a healthcare professional before use

Potential issues

Side effects and interactions with other medications

Upstream product

• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 108-69-0 3,5-dimethylaminoaniline 
• 116861-31-5 tert-butyl N-(3-chloropropyl)carbamate 
• 198218-71-2 (S)-N-(tert-butoxycarbonyl)-2-(2-phenyl)ethenylpyrrolidine 
• 220926-85-2 N-(tert-butoxycarbonyl)-N-(3-trans-phenyl-2-propenyl)-3-chloropropylamine 
• 350022-46-7 N-(tert-butoxycarbonyl)-2-(2-phenylethenyl)pyrrolidine 
• 86953-79-9 tert-butyl pyrrolidine-1-carboxylate 
• 15761-39-4 N-tert-butoxycarbonyl-proline 

Downstream Products

• 1092577-93-9 C₁₇H₂₆N₂O₂S 
• 1092577-91-7 C₁₇H₂₆N₂O₂S 
• 1361321-96-1 (S)-1-(4-methoxy-benzenesulfonyl)-pyrrolidine-2-carboxylicacid (3,5-dimethyl-phenyl)-amide 
• 220037-58-1 (S)-Pyrrolidine-2-carboxylic acid (3,5-dimethyl-phenyl)-amide 

Relevant articles and documents

On-bead combinatorial approach to the design of chiral stationary phases for HPLC

A library of 36 L-amino acid anilides, which are potential selectors for chiral HPLC, was synthesized in solution and attached to functionalized macroporous polymer beads. The best selector from the library was identified by a deconvolution process using

Chiral Lewis Base-Catalyzed, Enantioselective Reduction of Unprotected β-Enamino Esters with Trichlorosilane

Catalytic asymmetric reduction of N-unsubstituted β-enamino esters represents a major challenge for asymmetric catalysis. In this paper, the first organocatalytic system that could be used for the asymmetric hydrosilylation of N-unsubstituted β-enamino esters has been developed. Using N-tert-butylsulfinyl-L-proline-derived amides and L-pipecolinic acid-derived formamides as catalyst, a broad range of β-aryl- and β-alkyl-substituted free β-amino esters could be prepared with high yields and enantioselectivities. The practicality was illustrated by the gram-scale asymmetric synthesis of ethyl (R)-3-amino-3-phenylpropanoate and isopropyl (S)-3-amino-4-(2,3,5-trifluorophenyl)butanoate. The resulting product can be smoothly transformed to the FDA approved medicines dapoxetine and sitagliptin in a short synthetic route.

Structure-activity relationship, biological, and pharmacological characterization of the proline sulfonamide ACT-462206: A potent, brain-penetrant dual orexin 1/orexin 2 receptor antagonist

The orexin system consists of two G-protein-coupled receptors, the orexin 1 and orexin 2 receptors, widely expressed in diverse regions of the brain, and two peptide agonists, orexin A and orexin B, which are produced in a small assembly of neurons in the lateral hypothalamus. The orexin system plays an important role in the maintenance of wakefulness. Several compounds (almorexant, SB-649868, suvorexant) have been in advanced clinical trials for treating primary insomnia. ACT-462206 is a new, potent, and selective dual orexin receptor antagonist (DORA) that inhibits the stimulating effects of the orexin peptides at both the orexin 1 and 2 receptors. It decreases wakefulness and increases non-rapid eye movement (non-REM) and REM sleep while maintaining natural sleep architectures in rat and dog electroencephalography/electromyography (EEG/EMG) experiments. ACT-462206 shows anxiolytic-like properties in rats without affecting cognition and motor function. It is therefore a potential candidate for the treatment of insomnia.