155322-81-9

Basic information

• Product Name: (S)-2-amino-N-benzyl-2-phenylacetamide
• Synonyms: (S)-2-amino-N-benzyl-2-phenylacetamide
• CAS NO: 155322-81-9
• Molecular Weight: 240.305
• Mol File: 155322-81-9.mol

Chemical Properties

• CAS DataBase Reference: (S)-2-amino-N-benzyl-2-phenylacetamide(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-amino-N-benzyl-2-phenylacetamide(155322-81-9)
• EPA Substance Registry System: (S)-2-amino-N-benzyl-2-phenylacetamide(155322-81-9)

Safety Data

• Hazardous Substances Data: 155322-81-9(Hazardous Substances Data)

Upstream product

• 100-46-9 benzylamine 
• 146118-22-1 Z-PhGly-OSu 
• 201152-47-8 Boc-Phg-OSu 
• 2900-27-8 (2S)-2-[(tert-butoxycarbonyl)amino]-2-phenylethanoic acid 
• 5491-18-9 (S)-N-(benzyloxycarbonyl)phenylglycine 
• 2935-35-5 (S)-2-phenylglycine 
• 117422-78-3 (S)-tert-butyl (2-(benzylamino)-2-oxo-1-phenylethyl)carbamate 

Downstream Products

• 155220-85-2 (3S,5R,8aR)-1-Benzyl-5-ethyl-3-phenyl-octahydro-imidazo[1,2-a]pyridine 
• 155220-83-0 (3S,5R,8aR)-1-Benzyl-5-methyl-3-phenyl-octahydro-imidazo[1,2-a]pyridine 
• 155322-82-0 (3R,5S,8aS)-1-Benzyl-5-methyl-3-phenyl-octahydro-imidazo[1,2-a]pyridine 
• 155220-78-3 [(S)-1-Benzyl-4-phenyl-imidazolidin-(2E)-ylidene]-acetic acid ethyl ester 

Relevant articles and documents

SAR evolution towards potent C-terminal carboxamide peptide inhibitors of Zika virus NS2B-NS3 protease

Zika virus (ZIKV) is a member of the Flaviviridae family that can cause neurological disorders and congenital malformations. The NS2B-NS3 viral serine protease is an attractive target for the development of new antiviral agents against ZIKV. We report here a SAR study on a series of substrate-like linear tripeptides that inhibit in a non-covalent manner the NS2B-NS3 protease. Optimization of the residues at positions P1, P2, P3 and of the N-terminal and C-terminal portions of the tripeptide allowed the identification of inhibitors with sub-micromolar potency with phenylglycine as arginine-mimicking group and benzylamide as C-terminal fragment. Further SAR exploration and application of these structural changes to a series of peptides having a 4-substituted phenylglycine residue at the P1 position led to potent compounds showing double digit nanomolar inhibition of the Zika protease (IC50 = 30 nM) with high selectivity against trypsin-like proteases and the proteases of other flavivirus, such as Dengue 2 virus (DEN2V) and West Nile virus (WNV).

Asymmetric phosphoric acid-catalyzed four-component Ugi reaction

The Ugi reaction constructs a-acylaminoamide compounds by combining an aldehyde or ketone,an amine,a carboxylic acid,and an isocyanide in a single flask.Its appealing features include inherent atom and step economy together with the potential to generate products of broad structural diversity.However,control of the stereochemistry in this reaction has proven to be a formidable challenge.We describe an efficient enantioselective four-component Ugi reaction catalyzed by a chiral phosphoric acid derivative that delivers more than 80 a-acylaminoamides in good to excellent enantiomeric excess.Experimental and computational studies establish the reaction mechanism and origins of stereoselectivity.

l-tert-Leucine-Derived AmidPhos-Silver(I) Chiral Complexes for the Asymmetric [3+2] Cycloaddition of Azomethine Ylides

The l-tert-leucine-derived AmidPhos/silver(I) catalytic system has been developed for the asymmetric [3+2] cycloaddition of azomethine ylides with electronic-deficient alkenes with or without Et3N. Under optimal conditions, highly functionalized endo-4-pyrrolidines were obtained with modest to high yields (up to 99% yield) and enantioselectivities (up to 98% ee).

Mechanistic implications of the enantioselective addition of alkylzinc reagents to aldehydes catalyzed by nickel complexes with α-amino amide ligands

The enantioselective alkylation of aldehydes catalysed by nickel(ii)-complexes derived from α-amino amides was studied by means of density functional theory (DFT) and ONIOM (B3LYP:UFF) calculations. A mechanism was proposed in order to investigate the origin of enantioselectivity. The chirality-determining step for the alkylation was the formation of the intermediate complexes with the involvement of a 5/4/4-fused tricyclic transition state. The predominant products predicted theoretically were of (S)-configuration, in good agreement with experimental observations. The scope of the reaction was examined and high yields and enantioselectivities were observed for the enantioselective addition of Et2Zn and Me2Zn to aromatic and aliphatic aldehydes.

B(OCH2CF3)3-mediated direct amidation of pharmaceutically relevant building blocks in cyclopentyl methyl ether

The use of B(OCH2CF3)3 for mediating direct amidation reactions of a wide range of pharmaceutically relevant carboxylic acids and amines is described, including numerous heterocycle-containing examples. An initial screen of solvents for the direct amidation reaction suggested that cyclopentyl methyl ether, a solvent with a very good safety profile suitable for use over a wide temperature range, was an excellent replacement for the previously used solvent acetonitrile. Under these conditions amides could be prepared from 18 of the 21 carboxylic acids and 18 of the 21 amines examined. Further optimisation of one of the low yielding amidation reactions (36% yield) via a design of experiments approach enabled an 84% yield of the amide to be obtained.

C2 symmetrical nickel complexes derived from α-amino amides as efficient catalysts for the enantioselective addition of dialkylzinc reagents to aldehydes

A series of C2 symmetrical 1:2 Ni:L complexes derived from α-amino amides were studied for the enantioselective addition of dialkylzinc reagents to aldehydes. Different structural elements on the ligands seem to play an important role in determining the observed enantioselectivity. Through optimization of structure and reaction conditions, the best ligand provided secondary alcohols in excellent yields (up to 98%) and enantioselectivity of up to 99% ee for (R)-enantiomer. A transition state model has been proposed to explain the observed enantioselectivities based on computational calculations at the DFT level. Very interestingly, calculations suggest a coordination model of the aldehyde to the metal complex through association of a lone pair of the carbonyl oxygen to the hydrogen atom of an amino group.

Discovery of potent and orally active MTP inhibitors as potential anti-obesity agents

We have successfully identified a number of novel MTP inhibitors with single digit nanomolar potency. Analogues 10aq and 10dq demonstrated in vivo efficacy in a murine gut retention assay.

A new route to homochiral piperidines

The synthesis of an enantiomeric pair of enaminoesters from phenylglycine is described. Conjugate addition to α,β-enones, reductive cyclization-fragmentation to octahydroimidazopyridines and further reduction to remove the auxiliary atoms, completes a new route to homochiral piperidines in which the enaminoesters function as homochiral 'ethanal enamines'.

Design and synthesis of HIV protease inhibitors. Variations of the carboxy terminus of the HIV protease inhibitor L-682,679

A series of tetrapeptide analogues of 1 (L-682,679), in which the carboxy terminus has been shortened and modified, was prepared and their inhibitory activity measured against the HIV protease in a peptide cleavage assay. Selected examples were tested as inhibitors of virus spread in cell culture. Compound 12 was a 10-fold more potent enzyme inhibitor than 1 in vitro and 30-fold more potent in inhibiting the viral spread in cells.