52913-16-3

Basic information

• Product Name: (S)-4-METHOXY-N-PHTHALOXYLTYROSINE
• Synonyms: (S)-4-METHOXY-N-PHTHALOXYLTYROSINE;1,3-DIHYDRO-A-[(4-METHOXYPHENYL)METHYL]-1,3-DIOXO-, (S)-
• CAS NO: 52913-16-3
• Molecular Formula: C₁₈H₁₅NO₅
• Molecular Weight: 325.32
• Mol File: 52913-16-3.mol

Chemical Properties

• Melting Point: 127-129 °C
• Appearance: /
• CAS DataBase Reference: (S)-4-METHOXY-N-PHTHALOXYLTYROSINE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-4-METHOXY-N-PHTHALOXYLTYROSINE(52913-16-3)
• EPA Substance Registry System: (S)-4-METHOXY-N-PHTHALOXYLTYROSINE(52913-16-3)

Safety Data

• Hazardous Substances Data: 52913-16-3(Hazardous Substances Data)

Usage

Uses

Used in Medicinal Chemistry:
(S)-4-METHOXY-N-PHTHALOXYLTYROSINE is used as a building block for the synthesis of natural products due to its unique structure and potential biological activities, contributing to the development of new pharmaceutical compounds.
Used in Drug Development:
(S)-4-METHOXY-N-PHTHALOXYLTYROSINE is used as a scaffold for the development of new bioactive compounds, leveraging its potential to inhibit enzymes and its applicability in creating novel therapeutic agents.
Used in Enzyme Inhibition Research:
(S)-4-METHOXY-N-PHTHALOXYLTYROSINE is used as an inhibitory agent in enzyme research, studying its ability to modulate enzyme activity and potentially leading to the discovery of new enzyme-targeting drugs.

Upstream product

• 85-44-9 phthalic anhydride 
• 6230-11-1 O-Methyltyrosine 
• 696-62-8 para-iodoanisole 
• 4192-28-3 Phth-L-Ala-OH 
• 22509-74-6 N-ethoxycarbonylphthalimide 

Downstream Products

• 111210-69-6 O-methyl-N-phthaloyl-(S)-tyrosyl chloride 
• 1290176-66-7 (2S)-2-methyl-1-[o-methyl-N-phthaloyl-(S)-tyrosyl]-1,2,3,4-tetrahydroquinoline 
• 1290176-67-8 (3S)-2,3-dihydro-3-methyl-4-[o-methyl-N-phthaloyl-(S)-tyrosyl]-4H-1,4-benzoxazine 
• 156624-78-1 methyl (S)-2-(1,3-dioxoisoindolin-2-yl)-3-(4-methoxyphenyl)propanoate 
• 1180130-18-0 C₂₁H₁₉NO₅S₂ 
• 136918-14-4 phthalimide 
• 830-09-1 3-(4'-methoxyphenyl)propenoic acid 
• 169614-59-9 2-[2-(4-methoxyphenyl)ethyl]-1H-isoindole-1,3(2H)-dione 
• 111320-47-9 6-Methoxy-2-phthalimido-1-indanon 
• 111210-76-5 (S)-(3,4-Dimethoxyphenyl)-<2-(4-methoxyphenyl)-1-phthalimidoethyl>-keton 

Relevant articles and documents

Ligand-Enabled β-C–H Arylation of α-Amino Acids Without Installing Exogenous Directing Groups

Herein we report acid-directed β-C(sp3)-H arylation of α-amino acids enabled by pyridine-type ligands. This reaction does not require the installation of an exogenous directing group, is scalable, and enables the preparation of Fmoc-protected unnatural amino acids in three steps. The pyridine-type ligands are crucial for the development of this new C(sp3)-H arylation.

Substituent effect on the stereoselectivity of acylation of racemic heterocyclic amines with N-phthaloyl-3-aryl-(S)-alanyl chlorides

The acylative kinetic resolution of racemic 2-methyl-1,2,3,4- tetrahydroquinoline and 2,3-dihydro-3-methyl-4H-1,4-benzoxazine using acyl chlorides of N-phthaloyl-(S)-phenylalanine, N-phthaloyl-3-(4-nitrophenyl)-(S)- alanine and N-phthaloyl-O-methyl-(S)-tyrosine as chiral resolving agents has been carried out. It is shown that the effectiveness of an acylative kinetic resolution depends on the electronic effects of substituents in the phenyl fragment of the acylating agent and increases as the electron-donating properties of the para-substituent (OMe > H > NO2) in phenyl fragment of N-phthaloyl-3-aryl-(S)-alanyl chlorides increase; conducting the process at a reduced temperature also contributes to an enhancement of the kinetic resolution.

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.