73048-81-4

Upstream product

• 35909-92-3 N-carbobenzoxy-L-phenylalanine methyl ester 
• 109453-49-8 (C₈H₇O₂)(NHCHCOO)(CH₂C₆H₅)(CO₂C₂H₅) 
• 1161-13-3 N-Cbz-L-Phe 
• 55740-07-3 (4S)-4-benzyl-5-oxo-1,3-oxazolidine-3-carboxylic acid benzyl ester 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 501-53-1 benzyl chloroformate 
• 1426580-54-2 (S)-benzyl 1-(2,3-dimethylbut-2-enyloxyamino)-1-oxo-3-phenylpropan-2-ylcarbamate 
• 3397-32-8 N-(benzyloxycarbonyl)-phenylalanine-N-hydroxysuccinimide ester 
• 62750-39-4 ((S)-1-Benzyl-2-imidazol-1-yl-2-oxo-ethyl)-carbamic acid benzyl ester 

Downstream Products

• 160167-63-5 (1R,4S)-N--2,3-oxazabicyclo<2.2.1>hept-5-ene 
• 160057-07-8 (1S,4R)-N--2,3-oxazabicyclo<2.2.1>hept-5-ene 
• 160167-69-1 cis-3(R)-(N-L-Phenylalanylamino)cyclopentan-1(S)-ol 
• 160057-09-0 cis-3(S)-(N-L-Phenylalanylamino)cyclopentan-1(R)-ol 
• 98714-71-7 methyl 2-[((2S)-2-[[(benzyloxy)carbonyl]amino]-3-phenylpropanoyl)amino]-2-methylpropanoate 
• 5703-58-2 L-Phenylalanine hydroxamate 

Relevant academic research and scientific papers

Amidation of carboxylic acids via the mixed carbonic carboxylic anhydrides and its application to synthesis of antidepressant (1S,2R)-tranylcypromine

Primary amidations of carboxylic acids 1 or 3 with NH4Cl in the presence of ClCO2Et and Et3N were developed to afford the corresponding primary amides in 22% to quantitative yields. Additionally, we have applied the amidation to the preparation of various amides containing hydroxamic acids and achieved the synthesis of (1S,2R)-tranylcypromine as an antidepressant medicine via Lossen rearrangement.

An Environmentally Sustainable Mechanochemical Route to Hydroxamic Acid Derivatives

An operationally simple, and cost efficient conversion of carboxylic acids into hydroxamic acid derivatives via a high-energy mechanochemical activation is presented. This ball milling methodology was applied to a wide variety of carboxylic acids dramatically improving purification issues associated with this class of molecules, which still remain one of the main bottlenecks of classical methodologies. (Figure presented.).

Exploration and pharmacokinetic profiling of phenylalanine based carbamates as novel substance P 1-7 analogues

The bioactive metabolite of Substance P, the heptapeptide SP1-7 (H-Arg-Pro-Lys-Pro-Gln-Gln-Phe-OH), has been shown to attenuate signs of hyperalgesia in diabetic mice, which indicate a possible use of compounds targeting the SP1-7 bi

Synthesis of hydroxamic acids by using the acid labile O-2-methylprenyl protecting group

Coupling of carboxylic acids with O-2-methylprenyl hydroxylamine provided O-protected hydroxamic acids, which could be deprotected by treatment with trifluoroacetic acid (TFA) in dichloromethane giving volatile by-products. Protected hydroxamic acids could be N-arylated or alkylated followed by deprotection to give N-substituted hydroxamic acids. Georg Thieme Verlag KG · Stuttgart · New York.

Amino acid derived amides and hydroxamic acids as ligands for asymmetric transfer hydrogenation in aqueous media

Amides and hydroxamic acids derived from α-amino acids were evaluated as ligands in combination with rhodium and iridium half-sandwich complexes in asymmetric transfer hydrogenation (ATH) of ketones. The reactions were performed in aqueous media using lithium formate as hydride source. The catalyst systems turned out to be highly efficient and ee's up to 90% were obtained.

Ethyl propiolate: A simple and convenient peptide coupling reagent

Ethyl propiolate has been used to activate N-protected amino acids to form a moderately activated vinyl-ester which aminolysis requires a catalytic amount of sodium bisulfite.

Simple one-flask method for the preparation of hydroxamic acids

(Matrix presented) A one-step conversion of carboxylic acids to hydroxamic acids under very mild conditions is described. This simple and efficient method has been applied for the synthesis of enantiopure hydroxamate of α-amino acids and peptides.

Effective synthesis of enantiopure hydroxamates by displacement of resin-bound esters with hydroxylamine

Enantiopure hydroxamic acids have been synthesized by nucleophilic displacement of carboxylates linked to oxime resin using hydroxylamine in a MeOH:CHCl3 solution.