53562-23-5

Basic information

• Product Name: Carbamic acid, [2-amino-2-oxo-1-(phenylmethyl)ethyl]-, phenylmethyl ester
• CAS NO: 53562-23-5
• Molecular Formula: C17H18N2O3
• Molecular Weight: 298.342
• Mol File: 53562-23-5.mol
• Article Data: 42

Chemical Properties

• CAS DataBase Reference: Carbamic acid, [2-amino-2-oxo-1-(phenylmethyl)ethyl]-, phenylmethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, [2-amino-2-oxo-1-(phenylmethyl)ethyl]-, phenylmethyl ester(53562-23-5)
• EPA Substance Registry System: Carbamic acid, [2-amino-2-oxo-1-(phenylmethyl)ethyl]-, phenylmethyl ester(53562-23-5)

Safety Data

• Hazardous Substances Data: 53562-23-5(Hazardous Substances Data)

Upstream product

• 4801-69-8 N-Benzyloxycarbonyl-L-phenylalanin- 
• 2578-84-9 N-benzyloxycarbonyl-L-phenylalanine p-nitrophenyl ester 
• 39608-52-1 benzyl carbonochloridate 
• 5241-58-7 L-Phenylalanine amide 
• 501-53-1 benzyl chloroformate 
• 108321-83-1 phenylalanine amide hydrochloride 
• 150-30-1 Phenylalanine 
• 3588-57-6 Z-DL-Phe-OH 
• 541-41-3 chloroformic acid ethyl ester 
• 65864-22-4 (S)-2-amino-3-phenylpropionamide hydrochloride 
• 35909-92-3 N-carbobenzoxy-L-phenylalanine methyl ester 
• 3397-32-8 N-(benzyloxycarbonyl)-phenylalanine-N-hydroxysuccinimide ester 
• 1161-13-3 N-Cbz-L-Phe 
• 6638-79-5 N,O-dimethylhydroxylamine*hydrochloride 

Downstream Products

• 17186-44-6 (S)-benzyl (1-(tert-butylamino)-1-oxo-3-phenylpropan-2-yl)carbamate 
• 62076-57-7 Z-Phe-ΔAla 
• 208665-37-6 2-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-3-oxo-butyric acid methyl ester 
• 208665-36-5 2-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-malonic acid dimethyl ester 
• 112037-34-0 Z-Phe-NCO 
• 876322-97-3 benzyl N-(1-benzyl-2-oxo-2-[1-(phenylsulfonyl)propylamino]ethyl)carbamate 
• 944913-89-7 (S)-2-(N-benzyl-N-benzyloxycarbonylamino)-3-phenyl-propionitrile 
• 944913-93-3 (S)-1-benzyl-4-[(Z)-tert-butyloxycarbonylmethylidene]-5-phenylmethyl-imidazolidin-2-one 
• 944914-09-4 (4S,5S)-4-(2-hydroxyethyl)-1,5-bis(phenylmethyl)-imidazolidin-2-one 
• 161450-33-5 (3R,6S)-6-benzyl-3-methyl-3-trifluoromethylpiperazine-2,5-dione 

Relevant articles and documents

Synthesis of Terminal Thiazoles from N-Protected Amino Acids and a Study of Their Antibacterial Activities

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Synthesis and Preclinical Evaluation of the First Carbon-11 Labeled PET Tracers Targeting Substance P1-7

Two potent SP1-7 peptidomimetics have been successfully radiolabeled via [11C]CO2-fixation with excellent yields, purity, and molar activity. l-[11C]SP1-7-peptidomimetic exhibited promising ex vivo biodistribution profile. Metabolite analysis showed that l-[11C]SP1-7-peptidomimetic is stable in brain and spinal cord, whereas rapid metabolic degradation occurs in rat plasma. Metabolic stability can be significantly improved by substituting l-Phe for d-Phe, preserving 70% more of intact tracer and resulting in better brain and spinal cord tracer retention. Positron emission tomography (PET) scanning confirmed moderate brain (1.5 SUV; peak at 3 min) and spinal cord (1.0 SUV; peak at 10 min) uptake for l- and d-[11C]SP1-7-peptidomimetic. A slight decrease in SUV value was observed after pretreatment with natural peptide SP1-7 in spinal cord for l-[11C]SP1-7-peptidomimetic. On the contrary, blocking using cold analogues of l- and d-[11C]tracers did not reduce the tracers' brain and spinal cord exposure. In summary, PET scanning of l- and d-[11C]SP1-7-peptidomimetics confirms rapid blood-brain barrier and blood-spinal-cord barrier penetration. Therefore, further validation of these two tracers targeting SP1-7 is needed in order to define a new PET imaging target and select its most appropriate radiopharmaceutical.

Carbohydrates as efficient catalysts for the hydration of α-amino nitriles

Directed hydration of α-amino nitriles was achieved under mild conditions using simple carbohydrates as catalysts exploiting temporary intramolecularity. A broadly applicable procedure using both formaldehyde and NaOH as catalysts efficiently hydrated a variety of primary and secondary susbtrates, and allowed the hydration of enantiopure substrates to proceed without racemization. This work also provides a rare comparison of the catalytic activity of carbohydrates, and shows that the simple aldehydes at the basis of chemical evolution are efficient organocatalysts mimicking the function of hydratase enzymes. Optimal catalytic efficiency was observed with destabilized aldehydes, and with difficult substrates only simple carbohydrates such as formaldehyde and glycolaldehyde proved reliable.