Racemetirosine

Base Information

• Chemical Name: Racemetirosine
• CAS No.: 658-48-0
• Deprecated CAS: 620-30-4,2304018-89-9
• Molecular Formula: C10H13NO3
• Molecular Weight: 195.218
• Hs Code.: 29225000
• European Community (EC) Number: 210-635-7
• UNII: X88TTO174Z
• DSSTox Substance ID: DTXSID90859529
• Nikkaji Number: J7.081E
• Wikipedia: AMPT
• Wikidata: Q15408417
• NCI Thesaurus Code: C74152
• ChEMBL ID: CHEMBL1330596
• Mol file: 658-48-0.mol

Synonyms:alpha Methyl p tyrosine;alpha Methyl para tyrosine;alpha Methyltyrosine;alpha Methyltyrosine Hydrochloride;alpha MPT;alpha-methyl- DL-Tyrosine;alpha-Methyl-p-tyrosine;alpha-Methyl-para-tyrosine;alpha-Methyltyrosine;alpha-Methyltyrosine Hydrochloride;alpha-Methyltyrosine, (+,-)-Isomer;alpha-Methyltyrosine, (D,L)-Isomer;alpha-Methyltyrosine, (L)-Isomer;alpha-MPT;Demser;DL-Tyrosine, alpha-methyl-;Hydrochloride, alpha-Methyltyrosine;Metirosine;Metyrosine;Racemetirosine

Chemical Property of Racemetirosine

Chemical Property:

• Appearance/Colour: off-white fine powder
• Vapor Pressure: 2.06E-06mmHg at 25°C
• Melting Point: >300 °C(lit.)
• Refractive Index: 1.575
• Boiling Point: 383.7 °C at 760 mmHg
• PKA: 2.29±0.16(Predicted)
• Flash Point: 185.9 °C
• PSA: 83.55000
• Density: 1.283 g/cm³
• LogP: 1.43700
• Storage Temp.: −20°C
• Solubility.: Aqueous Acid (Sparingly), Aqueous Base, Water (Slightly)
• XLogP3: -1.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 195.08954328
• Heavy Atom Count: 14
• Complexity: 211

Purity/Quality:

98%,99%, ^*data from raw suppliers

α-Methyl-D,L-tyrosine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CC1=CC=C(C=C1)O)(C(=O)O)N
• Recent ClinicalTrials: Oral SM-88 in Patients With Metastatic HR+/HER2- Breast Cancer
• Uses: A tyrosine hydroxylase inhibitor. An antihypertensive in pheochromocytoma.

Technology Process of Racemetirosine

There total 14 articles about Racemetirosine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.9%

L-methyltyrosine (672-87-7,5380-13-2) + α-methyl-p-tyrosine (672-86-6,5380-13-2) → 2-amino-3-(4-hydroxy-phenyl)-2-methyl-propionic acid (658-48-0,5380-13-2)

Guidance literature:

In tert-butyl methyl ether; at 20 ℃; for 1h;

Reference yield:

4-hydroxy-benzaldehyde (123-08-0,65581-83-1) → 2-amino-3-(4-hydroxy-phenyl)-2-methyl-propionic acid (658-48-0,5380-13-2)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂ / Pd-C / H₂O

2: NaH / toluene

3: (i) Raney-Ni, EtOH, (ii) H₂, PtO₂

With hydrogen; sodium hydride; palladium on activated charcoal; In water; toluene;

DOI:10.1021/jo01287a087

Reference yield:

2-{[1-(4-Chloro-phenyl)-meth-(Z)-ylidene]-amino}-3-(4-hydroxy-phenyl)-propionic acid ethyl ester (95157-52-1) → 2-amino-3-(4-hydroxy-phenyl)-2-methyl-propionic acid (658-48-0,5380-13-2)

Guidance literature:

Multi-step reaction with 3 steps

1: K₂CO₃ / acetone

2: 1.) solid KOH 2.) 1N HCl / 1.) Tetrabutylammonium iodide / 1.) acetonitrile, 0 to 15 deg C 2.) ether, 0 deg C_.

3: 1.) hydrogen 2.) 6N HCl / 1.) 10 percent Pd/C / 1.) ethanol

With hydrogenchloride; potassium hydroxide; hydrogen; potassium carbonate; palladium on activated charcoal; tetra-(n-butyl)ammonium iodide; In acetone;

DOI:10.1016/S0040-4039(00)88719-5

upstream raw materials:

2-Nitro-2-(4-hydroxybenzyl)propionsaeureethylester

2-Amino-3-(4-benzyloxy-phenyl)-2-methyl-propionic acid ethyl ester; hydrochloride

5-(4-hydroxy-benzyl)-5-methyl-imidazolidine-2,4-dione

2-amino-3-(4-methoxyphenyl)-2-methylpropionic acid

Downstream raw materials:

3-chloro-α-methyl-DL-tyrosine

3-bromo-α-methyl-DL-tyrosine

3,5-Dichloro-α-methyltyrosine

3,5-Dibromo-α-methyltyrosine

Refernces

• 1、 O'Donnell, Martin J.,LeClef, Brigitte,Rusterholz, David B.,Ghosez, Leon,Antoine, Jean-Pierre,Navarro, Mirtha. "α-METHYL AMINO ACIDS BY CATALYTIC PHASE-TRANSFER ALKYLATIONS". . p. 4259 - 4262. Retrieved 2007/10/02.