225918-60-5

Basic information

• Product Name: (S)-N-BOC-(2'-CHLOROPHENYL)GLYCINE
• Synonyms: (S)-N-Boc-(2'-chlorophenyl)glycine;2-(tert-butoxycarbonyl(2-chlorophenyl)amino)acetic acid;(2S)-2-{[(tert-butoxy)carbonyl]aMino}-2-(2-chlorophenyl)acetic acid;(S)-Boc-2-(2-Chlorophenyl)glycine;(2S)-2-(2-chlorophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid;N-Boc-S-2-Chlorophenylglycine
• CAS NO: 225918-60-5
• Molecular Formula: C13H16ClNO4
• Molecular Weight: 285.72
• Mol File: 225918-60-5.mol

Chemical Properties

• Boiling Point: 431.5 °C at 760 mmHg
• Flash Point: 214.8 °C
• Appearance: /
• Density: 1.272 g/cm³
• Storage Temp.: 2-8°C(protect from light)
• PKA: 3.26±0.10(Predicted)
• CAS DataBase Reference: (S)-N-BOC-(2'-CHLOROPHENYL)GLYCINE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-N-BOC-(2'-CHLOROPHENYL)GLYCINE(225918-60-5)
• EPA Substance Registry System: (S)-N-BOC-(2'-CHLOROPHENYL)GLYCINE(225918-60-5)

Safety Data

• Hazardous Substances Data: 225918-60-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(S)-N-BOC-(2'-CHLOROPHENYL)GLYCINE is used as a building block in organic synthesis for creating more complex molecules. Its specific structure and reactivity contribute to the development of advanced chemical compounds.
Used in Chemical Research:
In the field of chemical research, (S)-N-BOC-(2'-CHLOROPHENYL)GLYCINE serves as an important tool, facilitating the exploration of new chemical reactions and mechanisms.
Used in Pharmaceutical Synthesis:
(S)-N-BOC-(2'-CHLOROPHENYL)GLYCINE is utilized as a key intermediate in the synthesis of pharmaceuticals, playing a crucial role in the development of new drugs and bioactive compounds due to its unique properties.
Used in the Synthesis of Bioactive Compounds:
(S)-N-BOC-(2'-CHLOROPHENYL)GLYCINE is also employed in the synthesis of bioactive compounds, where its distinctive structure aids in the creation of molecules with potential therapeutic or biological activity.

Upstream product

• 225918-54-7 (S)-α-(2-chlorophenyl)-α-[(diphenylmethyl)amino]acetonitrile 
• 1021948-12-8 C₁₅H₂₀ClNO₃S 
• 24424-99-5 di-tert-butyl dicarbonate 
• 225918-58-1 (2S)-2-(2-chlorophenyl)glycine hydrochloride 
• 1253091-76-7 methyl 2-((tert-butoxycarbonyl)amino)-2-(2-chlorophenyl)acetate 
• 86169-24-6 2-amino-(2-chlorophenyl)ethanoic acid 
• 387845-99-0 N-benzyhydryl-(2-chlorobenzylidene)-amine 
• 141315-50-6 (S)-2-amino-(2-chlorophenyl)ethanoic acid 

Downstream Products

• 1176305-58-0 (S)-methyl 2-((tert-butoxycarbonyl)amino)-2-(2-chlorophenyl)acetate 
• 1366062-98-7 tert-butyl {1-(2-chlorophenyl)-2-[(2-methoxyethyl)-amino]-2-oxoethyl}carbamate 
• 1092069-07-2 C₂₇H₂₉ClN₄O₃ 
• 1443470-44-7 (R)-ethyl 2-((2-(2-amino-2-(2-chlorophenyl)acetyl)oxyethylcarbamoyloxy)methyl)-5,7-dimethyl-3-(2-(N-methylsulfamoyl)phenyl)-4-oxo-3,4-dihydroquinazoline-6-carboxylate 

Relevant articles and documents

Chemo-enzymatic approach to the synthesis of the antithrombotic clopidogrel

The (S)-2-chlorophenylglycine moiety is well recognized in the structure of (S)-clopidogrel, a known antithrombotic drug. We prepared an enantiomerically pure chiral building block via an enzyme-catalyzed resolution of (RS)-N-Boc-2-chlorophenylglycine methylester. The best results were obtained by means of an immobilized subtilisin, the cross-linked enzyme aggregate (Alcalase-CLEA). The high enantiomeric excess of the synthon obtained remained the same over the course of clopidogrel synthesis; the simplicity of the process makes this pathway suitable for large-scale preparation.

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).

Chemo-enzymatic dynamic kinetic resolution of amino acid thioesters

The L-forms of racemic-N-protected-β,γa,aunsaturated a-amino acid thioesters were found to be substrates for the subtilisin-catalysed hydrolysis to the corresponding acids. The D-enantiomer was continuously racemised in the presence of an organic base. The combined reactions in a biphasic system allowed the deracemisation of the amino acid derivatives based on a dynamic kinetic resolution. Excellent yields and enantioselectivities were achieved.