30925-12-3

Usage

Uses

Used in Pharmaceutical Industry:
N-Boc-(R)-a-(MethylaMino)-benzeneacetic acid is used as an intermediate in the synthesis of various pharmaceuticals for its ability to provide specific structural and functional properties to the final drug molecules. The N-Boc protecting group allows for selective reactions and controlled synthesis, ensuring the desired product formation.
Used in Agrochemical Industry:
In the agrochemical field, N-Boc-(R)-a-(MethylaMino)-benzeneacetic acid is utilized as a precursor in the development of agrochemicals, such as pesticides and herbicides. Its unique structure and reactivity contribute to the creation of effective and targeted agrochemical products.
Used in Fine Chemicals Production:
N-Boc-(R)-a-(MethylaMino)-benzeneacetic acid is employed as a key intermediate in the production of fine chemicals, which are high-purity, specialty chemicals used in various industries, including fragrances, flavors, and cosmetics. Its chiral nature and protecting group enable the synthesis of enantiomerically pure compounds, crucial for specific applications in these industries.

Upstream product

• 2900-27-8 (2S)-2-[(tert-butoxycarbonyl)amino]-2-phenylethanoic acid 
• 74-88-4 methyl iodide 
• 33125-05-2 Boc-D-Phg-OH 
• 1173806-01-3 (R)-methyl 2-(tert-butoxycarbonyl(methyl)amino)-2-phenylacetate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 875-74-1 (R)-phenylglycine 
• 124-38-9 carbon dioxide 
• 81616-14-0 tert-butyl N-benzyl-N-methylcarbamate 
• 2935-35-5 (S)-2-phenylglycine 
• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 

Downstream Products

• 1145835-55-7 (S)-2-[(2-1H-indol-3-ylacetyl)methylamino]-N-(4-isopropyl-phenyl)-2-phenylacetamide 
• 1145835-56-8 (R)-2-[(2-1H-indol-3-ylacetyl)methylamino]-N-(4-isopropyl-phenyl)-2-phenylacetamide 
• 1173806-05-7 (R)-tert-butyl 2-(isoquinolin-6-ylamino)-2-oxo-1-phenylethyl(methyl)carbamate 
• 1027565-10-1 {2-[3-(2,6-difluoro-benzyl)-5-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl]-1-phenyl-ethyl}-methyl-carbamic acid tert-butyl ester 
• 848121-56-2 {2-[5-benzo[1,3]dioxol-5-yl-3-(2,6-difluoro-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl]-1-phenyl-ethyl}-methyl-carbamic acid tert-butyl ester 
• 1027588-39-1 {2-[3-(2,6-difluoro-benzyl)-5-(3-methoxy-phenyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl]-1-phenyl-ethyl}-methyl-carbamic acid tert-butyl ester 
• 848121-46-0 3-[(2R)-[N-(tert-butoxycarbonyl)-N-methylamino]-2-phenylethyl]-1-(2,6-difluorobenzyl)-5-bromo-6-methyluracil 
• 152547-72-3 (R)-tert-butyl N-(2-hydroxy-1-phenylethyl)-N-methylcarbamate 
• 1361409-73-5 (S)-tert-butyl2-(4-fluorophenylamino)-2-oxo-1-phenylethyl-(methyl)carbamate 
• 1361409-71-3 (S)-2-(2-(1H-indol-3-yl)-N-methylacetamido)-N-(4-fluorophenyl)-2-phenylacetamide 
• 1374333-12-6 C₁₅H₁₅FN₂O 
• 1361409-74-6 C₂₀H₂₃N₅O₃ 
• 1208094-50-1 [(4-hydroxymethylphenylcarbamoyl)phenylmethyl]methylcarbamic acid tert-butyl ester 
• 136093-00-0 (-)-indolactam-Phg 

Relevant academic research and scientific papers

6-And 7-amino isoquinoline compounds and methods for making and using the same

6- and 7-amino isoquinoline compounds are provided that influence, inhibit or reduce the action of a kinase. Pharmaceutical compositions including therapeutically effective amounts of the 6- and 7-aminoisoquinoline compounds and pharmaceutically acceptabl

COMPOUNDS HAVING ACTIVITY IN INCREASING ION TRANSPORT BY MUTANT-CFTR AND USES THEREOF

The invention provides compositions, pharmaceutical preparations and methods for increasing activity of a mutant cystic fibrosis transmembrane conductance regulator protein (mutant-CFTR). The compositions pharmaceutical preparations and methods are useful for the study and treatment of disorders associated with mutant-CFTR, such as cystic fibrosis. The compositions and pharmaceutical preparations of the invention may comprise one or more phenylglycine-containing compounds of the invention, or an analog or derivative thereof

Formamides derived from N-methyl amino acids serve as new chiral organocatalysts in the enantioselective reduction of aromatic ketimines with trichlorosilane

Asymmetric reduction of N-aryl ketimines 1a-k, 43, and 45 with trichlorosilane can be catalyzed by new N-methyl l-amino acid-derived Lewis-basic organocatalysts, such as the valine-derived bisamide 3d (10 mol%), in toluene at room temperature with high enantioselectivity (≤92% ee). The structure-reactivity investigation shows that the product configuration is controlled by the nature of the side chain of the catalyst scaffold (e.g., i-Pr vs Me, as in 3d and 6e), so that catalysts of the same absolute configuration may induce the formation of the opposite enantiomers of the product. Arene-arene interactions between the catalyst and the incoming imine appear to be the prerequisite for asymmetric induction. This metal-free, organocatalytic protocol is competitive with the traditional, metal-catalyzed methodology.

Rapid access to N-Boc phenylglycine derivatives via benzylic lithiation reactions

We report a novel and efficient method for the enantioselective synthesis of N-Boc protected phenylglycines. Yields and enantiomeric ratios vary widely depending on the nature of the solvent, the substrate and on the method of forming the chiral complex. Results show that the major reaction pathway is an enantioselective deprotonation/substitution process. The enantioselectivity appears to be limited by the chiral discrimination ability of the s-BuLi-(-)-sparteine complex. The synthetic method described is one of the shortest route to useful enantioenriched N-Boc phenylglycine derivatives.

An expedient enantioselective synthesis of N-t-Boc-protected phenylsarcosine

Herein we describe a novel approach to the asymmetric synthesis of N-t-Boc-phenylsarcosine. The synthesis involves the enantioselective deprotonation at the benzylic position of N-t-Boc-N-methylbenzylamine 2 using the chiral complex s-BuLi/(-) sparteine 1

CCK-B agonist or antagonist activities of structurally hindered and peptidase-resistant Boc-CCK4 derivatives

Replacement of Met31 by (N-Me)Nle in CCK8 or CCK4 has been shown to improve the affinity and selectivity for CCK-B receptors. In order to obtain molecules with enhanced bioavailability, two novel series of protected tetrapeptides of the general formula Boc-Trp30-X-Asp-Y33 have been developed. Introduction of (N-Me)Nle and the bulky, aromatic naphthylalaninamide (Nal-NH2) in positions X and Y, respectively, does not greatly modify the affinity for guinea pig brain CCK-B receptors. In contrast, incorporation of hindering N-methyl amino acids such as (N-Me)Phe, (N-Me)Phg, or (N-Me)Chg, but not their non-methylated counterparts, in position X induced a large decrease in affinity for the CCK-B binding sites. Among the various peptides synthesized, Boc-[(N-Me)Nle31,1Nal- NH233]CCK4 (2) (K(I) = 2.8 nM), Boc-[Phg31,1Nal-NH233]CCK4 (15) (K(I) = 14 nM), and Boc-[Phg31,1Nal-N(CH3)233]CCK4 (17) (K(I) = 39 nM) displayed good affinities for brain CCK-B receptors and had good selectivity ratios. These pseudopeptides, in which the presence of unnatural and hydrophobic residues is expected to improve their penetration of the central nervous system, were shown to be very resistant to brain peptidases. Interestingly, whereas compounds 2 and 15 proved to be full agonists for rat hippocampal CCK-B receptors when measured in an electrophysiological assay, compound 17 behaved as a potent antagonist in the same test and displayed a good affinity in rat brain K(I)(CCK-B) = 51 nM as compared to the Merck antagonist L365,260, K(I)(CCK-B) = 12 nM. This illustrates a simple means to obtain CCK-B antagonists and suggests that the free, CONH2 group plays a critical role in the recognition of the agonist state of brain CCK-B receptors.

Synthesis of new indolactam analogues by microbial conversion

Ten indolactam congeners with L-Ala, Abu, γ,δ-Δ-Nva, Nva, Nle, tert-Leu, Leu, Ile, allo-Ile. Phg instead ofL-Val in (-)-indolactam-Val, were synthesized from their seco-compounds (N-methyl-L-amino acidyl-L-tryptophonol) by microbial conversion.