1204705-08-7

Basic information

• Product Name: (S)-α-amino-α-p-tolylacetic acid hydrochloride
• CAS NO: 1204705-08-7
• Molecular Weight: 201.653
• Mol File: 1204705-08-7.mol

Chemical Properties

• CAS DataBase Reference: (S)-α-amino-α-p-tolylacetic acid hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-α-amino-α-p-tolylacetic acid hydrochloride(1204705-08-7)
• EPA Substance Registry System: (S)-α-amino-α-p-tolylacetic acid hydrochloride(1204705-08-7)

Safety Data

• Hazardous Substances Data: 1204705-08-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
(S)-α-amino-α-p-tolylacetic acid hydrochloride is used as a catalyst and reagent in the pharmaceutical industry for the production of various drugs, including antihistamines and antidepressants. Its chiral nature allows for the creation of specific drug enantiomers, which can have different therapeutic effects and reduce potential side effects.
Used in Organic Chemistry Research:
In the field of organic chemistry, (S)-α-amino-α-p-tolylacetic acid hydrochloride serves as a valuable compound for research and development. It is used in the synthesis of other organic compounds, contributing to the advancement of chemical knowledge and the discovery of new substances with potential applications in various industries.
Safety and Handling:
Due to its high potency and reactivity, (S)-α-amino-α-p-tolylacetic acid hydrochloride must be handled and stored with care to prevent potential health hazards. Proper safety measures should be taken to ensure the safe use of (S)-α-amino-α-p-tolylacetic acid hydrochloride in both pharmaceutical and research settings.

Upstream product

• 1313219-13-4 (S,S)-α-p-tolyl-α-[1-(4-methoxyphenyl)ethylamino]acetonitrile hydrochloride 
• 104-87-0 4-methyl-benzaldehyde 
• 909038-80-8 2-[(S)-(3aS,9bR)-3a,9b-dihydro-3H-chromeno[4,3-c]isoxazol-1(4H)-yl(phenyl)methyl]-2-{[tert-butyl(dimethyl)silyl]oxy}malononitrile 
• 909038-81-9 methyl (2S)-(3aS,9bR)-3a,9b-dihydro-3H-chromeno[4,3-c]isoxazol-1(4H)-yl(phenyl)acetate 
• 909038-82-0 methyl (2S)-2-N-(tert-butoxycarbonylamino)-2-(4-methylphenyl)acetate 
• 479423-27-3 tert-butyl (phenylsulfonyl(p-tolyl)methyl)carbamate 
• 774225-33-1 N-Boc-amino-(4'-methylphenyl)acetonitrile 
• 111652-11-0 tert-Butoxycarbonylamino-p-tolyl-acetic acid tert-butyl ester 

Downstream Products

• 60241-94-3 N-benzoyl-C-(4-methylphenyl)-glycine 

Relevant articles and documents

Synthesis of α-amino acid precursors directly from aldehydes using masked acyl cyanide reagents and N,O-dialkylated hydroxylamines

A synthetic methodology for the synthesis of α-amino acid precursors directly from the corresponding aldehydes using N,O-dialkylated hydroxylamines and masked acyl cyanide (MAC) reagents was developed. The one-pot reaction can be carried out under mild co

A convenient synthesis of N-boc-protected α-aminonitriles from α-amidosulfones

Synthesis of N-Boc-protected α-aminonitriles starting from N-Boc-protected α-aminosulfones is described. Treatment of the sulfone with two equivalents of potassium cyanide in 2-propanol or dichloromethane- H2O under phase transfer condition affords crystalline N-Boc-protected α-aminonitriles in good yield. Hydrolysis of the aminonitriles provides a convenient access to racemic α-amino acids.

Asymmetric strecker synthesis of α-arylglycines

A practically simple three-component Strecker reaction for the asymmetric synthesis of enantiopure α-arylglycines has been developed. Addition of a range of aryl-aldehydes to a solution of sodium cyanide and (S)-1-(4- methoxyphenyl)ethylamine affords highly crystalline (S,S)-α-aminonitriles that are easily obtained in diastereomerically pure form. Heating the resultant (S,S)-α-aminonitriles in 6 M aqueous HCl at reflux resulted in cleavage of their chiral auxiliary fragments and concomitant hydrolysis of their nitrile groups to afford enantiopure (S)-α-arylglycines. The enantiopurities of these (S)-α-arylglycines were determined via derivatization of their corresponding methyl esters with 2-formylphenylboronic acid and (S)-BINOL, followed by 1H NMR spectroscopic analysis of the resultant mixtures of diastereomeric iminoboronate esters.

A practical synthesis of optically active arylglycines via catalytic asymmetric Strecker reaction

A practical procedure for catalytic asymmetric synthesis of optically active arylglycine derivatives via optically active α-aminonitriles has been developed. The N-benzhydryl α-arylaminonitrile intermediates were prepared in excellent yield (89-99%) and enantiomeric purity (96 to >98% ee) by enantioselective cyanation of aldimines with TMSCN/iPrOH in the presence of 2.5 mol % of an easily prepared Ti/chiral amino alcohol complex at 0 °C, without requiring slow addition of the cyanating agent. The easily racemized α-aminonitrile intermediates were efficiently hydrolyzed by an aqueous HCl/TFA mixture to give the arylglycine derivatives in good yield (60-92%) and moderate to excellent enantiomeric purity (85-98% ee).

Use of the chiral pool - Practical asymmetric organocatalytic strecker reaction with quinine

An efficient, organocatalytic enantiose-lective synthesis of N-arylsulfonyl α-amino nitriles from the corresponding α-amido sulfones has been developed. This quinine-catalyzed Strecker reaction provides the corresponding cyanated products in good yields a

Synthesis of α-Amino Acids by Reaction of t-Butyl N-(t-Butoxycarbonyl)iminoacetate With C-Nucleophiles

The reaction of t-butyl N-(t-butoxycarbonyl)iminoacetate with Grignard reagents or enamines yields N-(t-butoxycarbonyl)amino acid t-butyl esters which can be easily converted into the free amino acids by treatment with acids.