111524-98-2

Basic information

• Product Name: (2S)-2-phenyl-2-(tosylamino)acetic acid
• Synonyms: (2S)-2-phenyl-2-(tosylamino)acetic acid
• CAS NO: 111524-98-2
• Molecular Weight: 305.354
• Mol File: 111524-98-2.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: (2S)-2-phenyl-2-(tosylamino)acetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-2-phenyl-2-(tosylamino)acetic acid(111524-98-2)
• EPA Substance Registry System: (2S)-2-phenyl-2-(tosylamino)acetic acid(111524-98-2)

Safety Data

• Hazardous Substances Data: 111524-98-2(Hazardous Substances Data)

Upstream product

• 62977-82-6 benzyl oxo(phenyl)acetate 
• 611-73-4 Benzoylformic acid 
• 98-86-2 acetophenone 
• 875-74-1 (R)-phenylglycine 
• 98-59-9 p-toluenesulfonyl chloride 
• 32462-30-9 (S)-hydroxyphenylglycine 
• 887113-22-6 (S)-2-phenyl-2-(tosylamino)acetaldehyde 
• 1002115-88-9 N-[cyano(phenyl)methyl]-4-methylbenzenesulfonamide 
• 176298-46-7 2-hydroxy-3-(4-methyl benzenesulfonylamino)-3-phenyl-propionic acid methyl ester 
• 350479-90-2 (S,E)-N-benzylidene-4-methylbenzenesulfinamide 
• 103-26-4 Methyl cinnamate 
• 127-65-1 chloroamine-T 
• 51608-60-7 N-(benzylidene)-p-methylbenzenesulfonamide 
• 616241-17-9 (S)-2-[phenyl-(toluene-4-sulfonylamino)methyl]acrylic acid phenyl ester 

Downstream Products

• 2935-35-5 (S)-2-phenylglycine 
• 875-74-1 (R)-phenylglycine 
• 111524-99-3 N-(p-tolylsulfonyl)-α-phenylglycine chloride 
• 111047-54-2 (S)-methyl 2-((4-methylphenyl)sulfonamido)-2-phenylacetate 
• 1438047-98-3 C₂₃H₂₄N₂O₃S 
• 1019853-28-1 (S)-N-methoxy-N-methyl-2-(4-methylphenylsulfonamido)-2-phenylacetamide 
• 1324004-40-1 (S)-methyl 2-(N,4-dimethylphenylsulfonamido)-2-phenyl acetate 
• 53120-14-2 N,4-dimethyl-N-(1-phenylvinyl)benzene sulfonamide 

Relevant articles and documents

Pd(OAc)2-Catalyzed Asymmetric Hydrogenation of α-Iminoesters

An efficient Pd(OAc)2-catalyzed asymmetric hydrogenation of α-iminoesters was realized for the first time at 1 atm hydrogen pressure and room temperature. Pd(OAc)2, a less expensive Pd salt with low toxicity, was found to be the most suitable catalyst precursor rather than Pd(TFA)2 which is usually the catalyst of choice for homogeneous asymmetric hydrogenation. The chiral α-arylglycine fragments are widely found in many chiral products and bioactive molecules.

Development of Piperazinediones as dual inhibitor for treatment of Alzheimer's disease

Novel multifunctional 3,6-Diphenyl-1,4-bis(phenylsulfonyl)piperazine-2,5-dione derivatives were designed and synthesized for the treatment of Alzheimer's disease (AD). The designed scaffold has blood brain barrier penetrating ability, acetylcholinesterase (AChE) and matrix metalloproteinase-2 (MMP-2) inhibition potential. Compounds 52 and 46 showed very significant inhibition against AChE, IC50 = 32.45 ± 0.044, 28.65 ± 0.029, BuChE, IC50 = 157.95 ± 0.264, 160.58 ± 0.082 and MMP-2, IC50 = 36.83 ± 0.015, 19.57 ± 0.005 (nM). In the enzyme kinetics study, lead molecule 46 showed non-competitive inhibition of AChE with Ki = 7 nM and competitive inhibition of MMP-2 with Ki = 20 nM. Compounds 52 and 46 inhibited AChE-induced Aβ aggregation at 20 μM. The compounds also exhibited in-vitro antioxidant potential in DPPH assay. Further, compound 46 was found to be a promising neuroprotective agent in MC65 cells. Lead molecule 46 significantly enhanced working memory in scopolamine induced amnesia animal model at dose of 5 mg/kg dose. The mitochondrial membrane potential was restored in animals when treated with compounds 52 and 46.

Asymmetric synthesis of N-tosyl amino acids from N-sulfinyl α-amino-1,3-dithioketals

Hydrolysis of diastereomerically pure N-sulfinyl α-amino-1,3- dithianes with 1,3-dibromo-5,5-dimethylhydantoin gives N-tosyl α-amino aldehydes which when subjected to a Pinnick-type oxidation gave N-tosyl α-amino acids without epimerization.