Sobetirome

Base Information

• Chemical Name: Sobetirome
• CAS No.: 211110-63-3
• Molecular Formula: C20H24O4
• Molecular Weight: 328.40200
• UNII: XQ31741E9Q
• DSSTox Substance ID: DTXSID60891557
• Nikkaji Number: J1.430.329D
• Wikidata: Q27088838
• NCI Thesaurus Code: C81539
• Pharos Ligand ID: JLGSR8MBAQ5Y
• Metabolomics Workbench ID: 150601
• ChEMBL ID: CHEMBL107400
• Mol file: 211110-63-3.mol

Synonyms:(3,5-dimethyl-4-(4'-hydoxy-3'-isopropylbenzyl)phenoxy)acetic acid;GC 1 compound;GC-1;GC-1 compound;GC-1 cpd;QRX 431;QRX-431;QRX431;sobetirome

Chemical Property of Sobetirome

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 122 - 124°C
• Boiling Point: 510.156oC at 760 mmHg
• PKA: 3.22±0.10(Predicted)
• Flash Point: 178.945oC
• PSA: 66.76000
• Density: 1.152g/cm3
• LogP: 4.18660
• Storage Temp.: -20°C
• Solubility.: DMSO: soluble10mg/mL, clear
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 328.16745924
• Heavy Atom Count: 24
• Complexity: 396

Purity/Quality:

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

GC 1 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=CC(=C1CC2=CC(=C(C=C2)O)C(C)C)C)OCC(=O)O
• Recent ClinicalTrials: Safety, Pharmacokinetics and Pharmacodynamics of NV1205 in Pediatric Male Subjects With Adrenoleukodystrophy
• Recent EU Clinical Trials: Phase I/II, Open-Label, Dose Escalation Study of the Safety, Pharmacokinetics, and Pharmacodynamics of NV1205 in Pediatric Male Subjects with Childhood Cerebral Adrenoleukodystrophy (CCALD)
• Uses: GC 1 is a high affinity thyroid receptor α (TRα) and TRβ agonist.

Technology Process of Sobetirome

There total 14 articles about Sobetirome 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: 79.0%

[3,5-dimethyl-4-(3'-isopropyl-4'-O-methoxymethylbenzyl)phenoxy]tert-butylacetate (328236-48-2) → sobetirome (211110-63-3)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; isopropyl alcohol; at 20 ℃; for 2h;

DOI:10.1016/S0960-894X(00)00531-X

Reference yield:

(4-benzyloxy-3-isopropyl-phenyl)-(2,6-dimethyl-4-triisopropylsilanyloxy-phenyl)-methanol (904925-63-9) + Benzyl bromoacetate (5437-45-6) → sobetirome (211110-63-3)

Guidance literature:

(4-benzyloxy-3-isopropyl-phenyl)-(2,6-dimethyl-4-triisopropylsilanyloxy-phenyl)-methanol; With tetrabutyl ammonium fluoride; In tetrahydrofuran;

Benzyl bromoacetate; With caesium carbonate; In N,N-dimethyl-formamide; at 40 ℃; for 4h;

With palladium 10% on activated carbon; hydrogen; acetic acid; at 20 ℃;

Reference yield:

4-bromo-3,5-dimethylphenol (7463-51-6) → sobetirome (211110-63-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 81 percent / imidazole / CH₂Cl₂ / 1 h

2.1: n-BuLi / tetrahydrofuran; pentane / 0.5 h / -78 °C

2.2: 70 percent / tetrahydrofuran; pentane / 2.5 h / -78 - 20 °C

3.1: n-BuLi / tetrahydrofuran; pentane / 0.5 h / -78 °C

3.2: 68 percent / tetrahydrofuran; pentane / 7 h / -78 - 20 °C

4.1: 80 percent / AcOH; H₂ / 10 percent Pd/C / ethanol / 12 h / 20 °C / 760 Torr

5.1: 90 percent / TBAF / tetrahydrofuran

6.1: 90 percent / Cs₂CO₃ / dimethylformamide / 0.5 h / 20 °C

7.1: 79 percent / 1N aq. HCl / propan-2-ol; tetrahydrofuran / 2 h / 20 °C

With 1H-imidazole; hydrogenchloride; n-butyllithium; tetrabutyl ammonium fluoride; hydrogen; caesium carbonate; acetic acid; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; pentane;

DOI:10.1016/S0960-894X(00)00531-X

upstream raw materials:

[3,5-dimethyl-4-(3'-isopropyl-4'-O-methoxymethylbenzyl)phenoxy]tert-butylacetate

[3,5-dimethyl-4-(3'-isopropyl-4'-nitroveratrylbenzyl)phenoxy]acetate

4-bromo-3,5-dimethylphenol

4-bromo-2-isopropyl-phenol

Refernces

• 1、 -. "Novel Phosphinic Acid-Containing Thyromimetics". Page/Page column 136. . Retrieved 2009/02/11.
• 2、 Chiellini, Grazia,Nguyen, Ngoc-Ha,Yoshihara, Hikari A.I.,Scanlan, Thomas S.. "Improved synthesis of the iodine-free thyromimetic GC-1". . p. 2607 - 2611. Retrieved 2007/10/03.