111210-66-3

Upstream product

• 85-44-9 phthalic anhydride 
• 1012-05-1 D,L-homophenylalanine 
• 100-39-0 benzyl bromide 
• 4443-40-7 phthaloylasparic anhydride 
• 103-63-9 1-phenyl-2-bromoethane 
• 5463-92-3 2-acetylamino-2-phenylethylmalonic acid diethyl ester 

Downstream Products

• 140408-88-4 N-phthaloylhomophenylalanine methyl ester 
• 60504-99-6 2-Phthalimido-1-tetralon 
• 111210-75-4 (3,4-Dimethoxyphenyl)-(3-phenyl-1-phthalimidopropyl)-keton 
• 111210-68-5 N-Phthaloylhomophenylalanylchlorid 
• 138780-02-6 trans-N-phthaloyl-α,β-methanophenylalanine methyl ester 
• 138780-02-6 cis-N-phthaloyl-α,β-methanophenylalanine methyl ester 
• 140408-89-5 γ-bromo-N-phthaloylhomophenylalanine methyl ester 
• 140408-91-9 γ-chloro-N-phthaloylhomophenylalanine methyl ester 

Relevant academic research and scientific papers

Synthesis of Quaternary α-Fluorinated α-Amino Acid Derivatives via Coordinating Cu(II) Catalytic α-C(sp3)-H Direct Fluorination

A coordinating, copper-catalyzed direct α-C(sp3)-H fluorination method has been developed to prepare vital quaternary α-fluorinated α-amino acid derivatives. A Cu(II) catalytic SET oxidative addition mechanism is proposed, involving a key fluoride-coupled Cu(II) charge transfer complex. The protocol can tolerate a rich variety of α-amino acids, for which the auxiliary group is removed in high yield and substituted for the direct preparation of dipeptide derivatives with detachable, single absolute configurations of the target compounds.

Palladium-Catalyzed Site-Selective Fluorination of Unactivated C(sp3)-H Bonds

The transition-metal-catalyzed direct C-H bond fluorination is an attractive synthetic tool toward the preparation of organofluorines. While many methods exist for the direct sp3 C-H functionalization, site-selective fluorination of unactivated sp3 carbons remains a challenge. Direct, highly site-selective and diastereoselective fluorination of aliphatic amides via a palladium-catalyzed bidentate ligand-directed C-H bond functionalization process on unactivated sp3 carbons is reported. With this approach, a wide variety of β-fluorinated amino acid derivatives and aliphatic amides, important motifs in medicinal and agricultural chemistry, were prepared with palladium acetate as the catalyst and Selectfluor as the fluorine source.

Bicyclic pyrrolyl amides as glucogen phosphorylase inhibitors

Heterocyclic amide derivatives, of formula (I): wherein —X-Y-Z- is selected from —S—CR4═CR5—, —CR4═CR5—S—, —O—CR4═CR5—, —CR4═CR5—O—, —N═CR4—S—, —S—CR4═N—, —NR6—CR4═CR5— and —CR4═CR5—NR6—; or a pharmaceutically acceptable salt or an in vivo hydrolysable ester thereof; (with provisos); possess glycogen phosphorylase inhibitory activity and accordingly have value in the treatment of disease states associated with increased glycogen phosphorylase activity. Processes for the manufacture of said heterocyclic amide derivatives and pharmaceutical compositions containing them are described.

DESIGN AND SYNTHETIC APPLICATIONS OF NEW HETEROMETALLACYCLES

The reaction of cyclic anhydrides with Ni(0) complexes lead to the formation of nickelacycles by oxidative addition followed by decarbonylation.The preparation of chiral nickelacycles from anhydrides derived from amino acids and their reactivity is described.The formation of new heteropalladacycles by C-H activation or transmetallation reactions and their reactivity will be also discussed.

Synthesis of Cyclopropyl Amino Acid Derivatives

Derivatives of α,β-methanovaline, α,β-methanophenylalanine and β-methyl-α,β-methanoalanine have been prepared by regioselective side-chain functionalization of suitably protected amino acid derivatives, followed by cyclization with either sodium hydride or 1,8-diazabicycloundec-7-ene.The approach used in this work illustrates a method for the synthesis of cyclopropyl amino acid derivatives which is complementary to existing procedures.

Intramolecular Friedel-Crafts Acylation of N-Phthaloyl-Substituted Arylalanyl and Homophenylalanyl Chlorides

N-Phthaloyl-protected arylalanyl and homophenylalanyl chlorides 5 are acylated intramolecularly to 2-phthalimido-1-indanones 6 and -1-tetralone (6d) with AlCl3 (two-fold molar amounts) or catalytic amounts of FeCl3.The cycloacylation to the tetralone 6d with AlCl3 or FeCl3 proceeds without racemisation in very good yields, whereas the cycloacylation to the indanone 6a with FeCl3 gives rise to racemisation.Mixed anhydrides 11 of N-phthaloyl-α-amino acids and trifluoromethanesulfonate were prepared from the N-phthaloylamino acid chlorides and silver triflate.Acylation of arenes 12 with 11a as well as cycloaddition of (S)-O-methyl-N-phthaloyltyrosine triflate can be achieved without racemisation and without a catalyst.