700-63-0

Basic information

• Product Name: 2-amino-2-phenylacetamide
• Synonyms: 2-Phenyl-2-aminoacetamide;Aminophenylacetamide;2-azanyl-2-phenyl-ethanamide;DL-2-PhenylglycinaMide;)-alpha-Aminobenzeneacetamide;alpha-Amino-alpha-phenylacetamide;DL-alpha-Phenylglycine amide;DL-Phenylglycinamide
• CAS NO: 700-63-0
• Molecular Formula: C₈H₁₀N₂O
• Molecular Weight: 150.18
• EINECS: 211-849-3
• Mol File: 700-63-0.mol

Chemical Properties

• Melting Point: 130-131℃
• Boiling Point: 322.8±35.0 °C(Predicted)
• Appearance: /
• Density: 1.178±0.06 g/cm3(Predicted)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: DMSO (Sparingly, Heated, Sonicated), Methanol (Slightly)
• PKA: 15.61±0.50(Predicted)
• CAS DataBase Reference: 2-amino-2-phenylacetamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-amino-2-phenylacetamide(700-63-0)
• EPA Substance Registry System: 2-amino-2-phenylacetamide(700-63-0)

Safety Data

• RTECS: AB4390000
• Hazardous Substances Data: 700-63-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-amino-2-phenylacetamide is used as a key intermediate in the synthesis of enantiopure α-amino acids and amides, which are essential building blocks for the development of chiral drugs with improved therapeutic properties and reduced side effects.
Used in HIV Treatment:
2-amino-2-phenylacetamide is used in the preparation of HIV-1 reverse transcriptase inhibitors in the form of thiadiazole derivatives. These inhibitors play a crucial role in the treatment of HIV/AIDS by blocking the replication of the virus and preventing the progression of the disease.

InChI:InChI=1S/C8H10N2O/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7H,9H2,(H2,10,11)

Upstream product

• 6097-58-1 ethyl 2-phenyl-2-aminoacetate 
• 1086209-16-6 α-benzylideneamino-α-phenylacetamide 
• 16750-42-8 2-amino-2-phenylacetonitrile 
• 24461-61-8 (R)-Phenylglycine methyl ester 
• 51703-58-3 (RS)-phenylglycinamide hydrochloride 
• 19883-41-1 D-phenylglycine methyl ester hydrochloride 
• 53641-60-4 2-phenylglycinonitrile hydrochloride 
• 40966-78-7 2-(R)-2-phenyl-2-aminoacetyl chloride hydrochloride 
• 155385-85-6 (-)-1S-<(cyano phenyl methyl)amino>-2R-methyl-5R-(1-methylethenyl)-cyclohexane-1R,3R-dicarbonitrile 
• 51581-15-8 phenylglycine butyl ester hydrochloride 
• 72651-17-3 phenylglycine ethyl ester hydrochloride 
• 24461-61-8 phenylglycine methyl ester 
• 283157-18-6 2-(9-fluoroenylamino)-2-phenylacetamide 
• 2835-06-5 phenylglycin 

Downstream Products

• 875-74-1 (R)-phenylglycine 
• 100142-33-4 5,6-dimethyl-3-phenyl-1H-pyrazin-2-one 
• 127479-02-1 phenyl-5 piperazinetrione-2,3,6 
• 92850-20-9 α-amino-4-methyl-deoxybenzoin 
• 2882-18-0 3-phenyl-2(1H)-pyrazinone 
• 41270-61-5 3,5-diphenyl-1H-pyrazin-2-one 
• 855264-13-0 phenyl-thiobenzoylamino-acetic acid amide 
• 700-63-0 (R)-phenylglycine amide 
• 2935-35-5 (S)-2-phenylglycine 
• 5700-56-1 1,2-diaminophenylethane 
• 59801-51-3 2-(1,1-dioxo-1λ⁶-thiomorpholin-4-yl)-2-phenyl-acetamide 
• 25084-41-7 C₈H₈Cl₂N₂O 
• 5728-12-1 4-phenyl-[1,2,5]thiadiazol-3-ol 
• 127042-98-2 D-(-)-cyclohexylglycine amide 

Relevant articles and documents

Hybrid catalysis of 8-quinolinecarboxaldehyde and br?nsted acid for efficient racemization of α-amino amides and its application in chemoenzymatic dynamic kinetic resolution

The combination of 8-quinolinecarboxaldehyde and benzoic acid proved to be an effective catalyst system for the racemization of N-unprotected α-aryl- or α-alkyl-substituted α-amino amides. Application of this system to chemoenzymatic dynamic kinetic resolution provided an efficient access to enantiomerically pure N-acetyl-α-amino amides in good to high yields.

COMPLEMENT MODULATORS AND RELATED METHODS

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EGFR DIMER DISRUPTORS AND USE OF THE SAME

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Highly Active Chiral Dilithium(I) Binaphthyldisulfonate Catalysts for Enantio- And Chemoselective Strecker-Type Reactions

An enantioselective Strecker-type reaction of aldimines and ketimines was developed by using a chiral dilithium(I) binaphthyldisulfonate as a chiral acid-base cooperative catalyst. The present catalytic system features an extremely short reaction time (10 min to 4 h), unlike conventional catalytic systems. Along with the design of stronger chiral Li(I) Lewis acid catalysts, a highly reactive pentacoordinate silicate generated in situ could promote the reactions. In particular, instead of unstable N-Bn Strecker products, more stable N-CH2(9-anthryl) and N-CH2(1-naphthyl) Strecker products could be obtained in high yields with high enantioselectivities. By a switch of the present and previous catalyst systems, chemoselective cyanation to a ketoaldimine could be performed, respectively. Moreover, mechanistic investigations provided useful information regarding the active catalysts, catalytic cycles, and possible transition states.

RETRACTED ARTICLE: Chemoenzymatic Method for Enantioselective Synthesis of (R)-2-Phenylglycine and (R)-2-Phenylglycine Amide from Benzaldehyde and KCN Using Difference of Enzyme Affinity to the Enantiomers

In general, enzymatic and chemoenzymatic methods for asymmetric synthesis of α-amino acids are performed using highly enantioselective enzymes. The enzymatic reactions using α-aminonitrile as a starting material have been performed using reaction conditions apart from the chemical Strecker synthesis. We developed a new chemoenzymatic method for the asymmetric synthesis of α-amino acids from aldehydes and KCN by performing Strecker synthesis and nitrilase reaction in the same reaction mixture. Nitrilase AY487533 that showed rather low enantioselectivity in hydrolysis of 2-phenylglycinonitrile (2PGN) to 2-phenylglycine (2PG) was utilized in the hydrolysis of aminonitrile formed from benzaldehyde and KCN via 2PGN by Strecker synthesis, preferentially synthesizing (R)-2PG with more than 95 % yield and enantiomeric excess (ee). The method was also utilized for the synthesis of (R)-2-phenylglycine amide ((R)-2PGNH2) from benzaldehyde and KCN by the chemoenzymatic reaction in the presence of a mutated nitrilase AY487533W186A, which catalyzes the conversion of 2PGN to 2PGNH2.

Synthetic method for chiral alpha-aminoamide compounds

The invention provides a synthetic method for chiral alpha-aminoamide compounds, belongs to the technical field of organic synthetic methodology, and concretely relates to a synthetic method for chiral alpha-aminoamide compounds, wherein the method has a simple process, low costs and good economy. The method comprises the following steps: 1, performing ammonolysis: adding substituted chiral alpha-aminocarboxylate hydrochloride into concentrated ammonia water, performing stirring for 4-12h under a room temperature, wherein each 1mmol substituted chiral alpha-aminocarboxylate hydrochloride is corresponding to 2-8mL the concentrated ammonia water; 2, after a reaction is finished, performing distillation for removing ammonia water after the reaction to obtain crude products chiral alpha-aminoamide compounds; and 3, performing filtration on the obtained crude products chiral alpha-aminoamide compounds by adopting a manner of adding a solvent or performing purification on the obtained crude products chiral alpha-aminoamide compounds through a manner of column chromatography which uses ammonia water as a mobile phase to obtain the products chiral alpha-aminoamide compounds. Compared with the prior art, a large number of an ammonia gas for ammonolysis is not needed in the method, the process and post-treatment are simple, costs are low and reaction time is short.

A 6 - aminomethyl - 6, 11 - dihydro - 5H - dibenzo [b, e] for the preparation method

The invention relates to a preparation method of 6-aminomethyl-6,11-dihydro-5H-dibenzo[b,e]azepine, and belongs to the technical field of drug synthesis. The preparation method comprises the following steps: (1) converting phenylglycine methyl ester hydrochloride into benzene ammonia amide through amidation reactions; (2) converting benzene ammonia amide into 2-((2-amino-2-oxo-phenethyl)amino)methyl benzoate through coupling reactions; (3) converting 2-((2-amino-2-oxo-phenethyl)amino)methyl benzoate into 2-((2-(hydroxymethyl)phenyl)amino)-2-phenyl acetamide through reduction reactions; (4) converting 2-((2-(hydroxymethyl)phenyl)amino)-2-phenyl acetamide into 6-aminomethyl-6,11-dihydro-5H-dibenzo[b,e]azepine through alkylation reactions. The provided preparation method has the advantage that no cyanide is used.

Pharmacophore Mapping of Thienopyrimidine-Based Monophosphonate (ThP-MP) Inhibitors of the Human Farnesyl Pyrophosphate Synthase

The human farnesyl pyrophosphate synthase (hFPPS), a key regulatory enzyme in the mevalonate pathway, catalyzes the biosynthesis of the C-15 isoprenoid farnesyl pyrophosphate (FPP). FPP plays a crucial role in the post-translational prenylation of small GTPases that perform a plethora of cellular functions. Although hFPPS is a well-established therapeutic target for lytic bone diseases, the currently available bisphosphonate drugs exhibit poor cellular uptake and distribution into nonskeletal tissues. Recent drug discovery efforts have focused primarily on allosteric inhibition of hFPPS and the discovery of non-bisphosphonate drugs for potentially treating nonskeletal diseases. Hit-to-lead optimization of a new series of thienopyrimidine-based monosphosphonates (ThP-MPs) led to the identification of analogs with nanomolar potency in inhibiting hFPPS. Their interactions with the allosteric pocket of the enzyme were characterized by crystallography, and the results provide further insight into the pharmacophore requirements for allosteric inhibition.

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.

Enantioselective ammonolysis of phenylglycine methyl ester with lipase-pluronic nanoconjugate in tertiary butanol

Asymmetrical ammonolysis of (R)- and (S)-phenylglycine methyl ester was carried out by using a lipase (CALB)-polymer (Pluronic) nanoconjugate as the catalyst, displaying a 11-fold increased catalytic rate compared to the free CALB in tertiary butanol. Graphical Abstract: The asymmetrical ammonolysis of (R)- and (S)-phenylglycine methyl ester was accomplished using a lipase-Pluronic nanoconjugate, displaying a 11-fold higher catalytic rate compared to the free lipase.[Figure not available: see fulltext.]