Disodium (R,R)-5-(2-((2-(3-chlorophenyl)-2-hydroxyethyl)-amino)propyl)-1,3-benzodioxole-2,3-dicarboxylate

Base Information

• Chemical Name: Disodium (R,R)-5-(2-((2-(3-chlorophenyl)-2-hydroxyethyl)-amino)propyl)-1,3-benzodioxole-2,3-dicarboxylate
• CAS No.: 138908-40-4
• Deprecated CAS: 151126-84-0
• Molecular Formula: C20H18ClNO7•2Na
• Molecular Weight: 465.80
• UNII: CF9MRO9QWW
• DSSTox Substance ID: DTXSID6041004
• Wikidata: Q27275433
• ChEMBL ID: CHEMBL32590
• Mol file: 138908-40-4.mol

Synonyms:CL 316,243;CL 316243;CL-316,243;CL-316243;CL316,243;CL316243;disodium (R,R)-5-(2-((2-(3-chlorophenyl)-2-hydroxyethyl)-amino)propyl)-1,3-benzodioxole-2,3-dicarboxylate

Chemical Property of Disodium (R,R)-5-(2-((2-(3-chlorophenyl)-2-hydroxyethyl)-amino)propyl)-1,3-benzodioxole-2,3-dicarboxylate

Chemical Property:

• Vapor Pressure: 5.86E-20mmHg at 25°C
• Boiling Point: 689.5°Cat760mmHg
• Flash Point: 370.8°C
• PSA: 130.98000
• Density: g/cm³
• LogP: -0.04760
• Storage Temp.: room temp
• Solubility.: H2O: >10 mg/mL
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 6
• Exact Mass: 465.0567182
• Heavy Atom Count: 31
• Complexity: 578

Purity/Quality:

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

CL316243DisodiumSalt ^*data from reagent suppliers

Safty Information:

• Pictogram(s): A poison.
• Hazard Codes: A poison.

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(CC1=CC2=C(C=C1)OC(O2)(C(=O)[O-])C(=O)[O-])NCC(C3=CC(=CC=C3)Cl)O.[Na+].[Na+]
• Isomeric SMILES: C[C@H](CC1=CC2=C(C=C1)OC(O2)(C(=O)[O-])C(=O)[O-])NC[C@@H](C3=CC(=CC=C3)Cl)O.[Na+].[Na+]
• Uses: CL 316243 Disodium Salt is a potent and highly selective β3-adrenoceptor agonist. CL 316,243 hydrate has been used:as a β-agonists to inject mice and study its effect on the expression of mammalian major facilitator superfamily domain-containing protein (Mfsd2a)as an adrenergic agonist to stimulate adrenergic response in order to study the metabolic activity of brown, beige and white adipose tissues in mice as a β3-adrenergic agonist to inject mice for in vivo lipolytic challenge

Technology Process of Disodium (R,R)-5-(2-((2-(3-chlorophenyl)-2-hydroxyethyl)-amino)propyl)-1,3-benzodioxole-2,3-dicarboxylate

There total 14 articles about Disodium (R,R)-5-(2-((2-(3-chlorophenyl)-2-hydroxyethyl)-amino)propyl)-1,3-benzodioxole-2,3-dicarboxylate 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: 85.0%

5-{(R)-2-[(R)-5-(3-Chloro-phenyl)-2-oxo-oxazolidin-3-yl]-propyl}-benzo[1,3]dioxole-2,2-dicarboxylic acid diethyl ester (139013-14-2) → CL 316243 (138908-40-4,138908-41-5,138908-42-6,138908-43-7,139013-10-8,139014-45-2)

Guidance literature:

With sodium hydroxide;

DOI:10.1021/jm00094a025

Reference yield:

(S)-(-)-[2-(3,4-dimethoxyphenyl)-1-hydroxymethylethyl]carbamic acid tert-butyl ester (105779-71-3) → CL 316243 (138908-40-4,138908-41-5,138908-42-6,138908-43-7,139013-10-8,139014-45-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 86 percent / triethylamine

3: H₂ / Pd/C

4: N-(trimethylsilyl)acetamide / dimethylsulfoxide

6: 90 percent / BBr₃

7: 64 percent / K₂CO₃

8: 85 percent / aq. NaOH

With sodium hydroxide; hydrogen; boron tribromide; potassium carbonate; triethylamine; N-Trimethylsilylacetamide; palladium on activated charcoal; In dimethyl sulfoxide;

DOI:10.1021/jm00094a025

Reference yield:

(S)-(+)-2-tert-butoxycarbonylamino-3-(3,4-dimethoxyphenyl)propionic acid methyl ester (138908-56-2) → CL 316243 (138908-40-4,138908-41-5,138908-42-6,138908-43-7,139013-10-8,139014-45-2)

Guidance literature:

Multi-step reaction with 9 steps

1: 98 percent / LiBH₄

2: 86 percent / triethylamine

4: H₂ / Pd/C

5: N-(trimethylsilyl)acetamide / dimethylsulfoxide

7: 90 percent / BBr₃

8: 64 percent / K₂CO₃

9: 85 percent / aq. NaOH

With sodium hydroxide; lithium borohydride; hydrogen; boron tribromide; potassium carbonate; triethylamine; N-Trimethylsilylacetamide; palladium on activated charcoal; In dimethyl sulfoxide;

DOI:10.1021/jm00094a025

upstream raw materials:

5-{(R)-2-[(R)-5-(3-Chloro-phenyl)-2-oxo-oxazolidin-3-yl]-propyl}-benzo[1,3]dioxole-2,2-dicarboxylic acid diethyl ester

3-chlorophenacyl chloride

(R)-3,4-dimethoxy-α-methylbenzeneethanamine

(R)-meta-chlorostyrene oxide