61780-18-5

Basic information

• Product Name: Tyrosine, O-methyl-, methyl ester
• Synonyms: O-Methyl-tyrosin-methylester;O-Methyl-dl-tyrosin-methylester;2-Amino-3-(4-methoxy-phenyl)-propionic acid methyl ester;O-methyl-tyrosine methyl ester
• CAS NO: 61780-18-5
• Molecular Formula: C11H15NO3
• Molecular Weight: 209.245
• Mol File: 61780-18-5.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 158 °C (12 mmHg)
• CAS DataBase Reference: Tyrosine, O-methyl-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Tyrosine, O-methyl-, methyl ester(61780-18-5)
• EPA Substance Registry System: Tyrosine, O-methyl-, methyl ester(61780-18-5)

Safety Data

• Hazardous Substances Data: 61780-18-5(Hazardous Substances Data)

Upstream product

• 186581-53-3 diazomethane 
• 60-29-7 diethyl ether 
• 64-17-5 ethanol 
• 556-02-5 ?Tyr 
• 7732-18-5 water 
• 94790-24-6 (2R)-tert-butoxycarbonylamino-3-(4-methoxyphenyl)propionic acid methyl ester 
• 67-56-1 methanol 
• 39878-65-4 (R)-β-(4-methoxyphenyl)alanine 
• 3728-20-9 D-tyrosine methylester hydrochloride 
• 556-02-5 tyrosine 
• 76757-90-9 N-(tert-butoxycarbonyl)-D-tyrosine methyl ester 
• 70601-63-7 (D)-4-methoxyphenylalanine hydrochloride 
• 73594-87-3 methyl 2-chloro-3-(4-methoxyphenyl)propionate 
• 70887-29-5 4-methoxybenzyl iodide 

Downstream Products

• 400009-34-9 (R)-2-Dibenzylamino-3-(4-methoxy-phenyl)-propionic acid methyl ester 
• 1225439-14-4 methyl (R)-2-(3-1H-imidazol-4-ylpropionyl-amino)-3-(4-methoxyphenyl)propanoate 
• 1322877-65-5 trimethyl (2R,3S,4R,5S)-2-(4-methoxybenzyl)-5-(4-nitrophenyl)pyrrolidine-2,3,4-tricarboxylate 
• 1354521-78-0 methyl 5-formyl-6-hydroxy-2-(4-methoxyphenyl)-2H-benzo[b][1,4]oxazine-3-carboxylate 
• 473401-85-3 3,4-bis(4-methoxyphenyl)-1H-pyrrole-2,5-dicarboxylic acid dimethyl ester 
• 2234-38-0 3,4-bis(4-methoxyphenyl)-1H-pyrrole-2,5-dicarboxylic acid 
• 1186002-27-6 methyl α-(4-methoxybenzyl)diazoacetate 
• 120349-77-1 (Z)-(R)-4-tert-Butoxycarbonylamino-5-(4-methoxy-phenyl)-pent-2-enoic acid methyl ester 
• 120349-78-2 [(Z)-(R)-4-Hydroxy-1-(4-methoxy-benzyl)-but-2-enyl]-carbamic acid tert-butyl ester 
• 120349-75-9 (2R)-2-(tert-butoxycarbonyl)amino-3-(4-methoxyphenyl)propan-1-ol 
• 120349-79-3 (R)-2-(4-Methoxy-benzyl)-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester 
• 139183-60-1 [(R)-1-Formyl-2-(4-methoxy-phenyl)-ethyl]-carbamic acid tert-butyl ester 
• 21399-39-3 (R)-2-(p-methoxyphenyl)methy-2,5-dihydropyrrole 

Relevant articles and documents

Discovery of BMS-986235/LAR-1219: A Potent Formyl Peptide Receptor 2 (FPR2) Selective Agonist for the Prevention of Heart Failure

Formyl peptide receptor 2 (FPR2) agonists can stimulate resolution of inflammation and may have utility for treatment of diseases caused by chronic inflammation, including heart failure. We report the discovery of a potent and selective FPR2 agonist and its evaluation in a mouse heart failure model. A simple linear urea with moderate agonist activity served as the starting point for optimization. Introduction of a pyrrolidinone core accessed a rigid conformation that produced potent FPR2 and FPR1 agonists. Optimization of lactam substituents led to the discovery of the FPR2 selective agonist 13c, BMS-986235/LAR-1219. In cellular assays 13c inhibited neutrophil chemotaxis and stimulated macrophage phagocytosis, key end points to promote resolution of inflammation. Cardiac structure and functional improvements were observed in a mouse heart failure model following treatment with BMS-986235/LAR-1219.

Synthesis of phenylalanine analogs

A straight forward synthesis of phenylalanine analogs is described. Cerium ammonium nitrate (CAN) mediated addition of azide to cinnamicester, followed by reaction with sodium acetate aff orded the α-azidocinnamate in moderate yield. Hydrogenation of α-azidocinnamate, followed by BOC, CBZ or Fmoc protection gave phenylalanine analogs. A new approach for synthesizing racemic p-boronophenylalanine analog was also explored.

An aldol-based approach to the synthesis of the antibiotic anisomycin

Chemical equation presented A new approach to the synthesis of the antibiotic anisomycin is reported that relies upon a key aldol disconnection. The glycolate aldol coupling proceeds in 75% yield and with >95% diastereoselectivity, which allows the 13-step synthesis to proceed in 35% overall yield.