5-(Carboxymethyl)-2-methoxyphenylboronic acid pinacol ester

Base Information

• Chemical Name: 5-(Carboxymethyl)-2-methoxyphenylboronic acid pinacol ester
• CAS No.: 1200443-26-0
• Molecular Formula: C₁₅H₂₁BO₅
• Molecular Weight: 292.14
• DSSTox Substance ID: DTXSID701143474
• Mol file: 1200443-26-0.mol

Synonyms:1200443-26-0;5-(Carboxymethyl)-2-methoxyphenylboronic acid pinacol ester;SCHEMBL2724971;DTXSID701143474;5-(Carboxymethyl)-2-methoxyphenylboronicacidpinacolester;2-[4-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetic acid;4-Methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzeneacetic acid

Chemical Property of 5-(Carboxymethyl)-2-methoxyphenylboronic acid pinacol ester

Chemical Property:

• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 292.1482039
• Heavy Atom Count: 21
• Complexity: 380

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=C(C=CC(=C2)CC(=O)O)OC

Technology Process of 5-(Carboxymethyl)-2-methoxyphenylboronic acid pinacol ester

There total 2 articles about 5-(Carboxymethyl)-2-methoxyphenylboronic acid pinacol ester 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: 96.0%

[4-methoxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-acetic acid methyl ester (944317-65-1) → 2-(4-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetic acid (1200443-26-0)

Guidance literature:

With water; lithium hydroxide; In methanol; at 25 ℃; for 0.5h;

DOI:10.1055/s-0029-1216937

Reference yield:

(3-bromo-4-methoxy-phenyl)-acetic acid (774-81-2) + bis(pinacol)diborane (73183-34-3) → 2-(4-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetic acid (1200443-26-0)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In 1,4-dioxane; at 100 ℃; for 17h;

Reference yield: 66.0%

2-(4-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetic acid (1200443-26-0) + C18H20N2O4*ClH (1200443-25-9) → methyl (S)-3-(4-hydroxyphenyl)-2-[(R)-2-{2-[4-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetamido}-2-phenylacetamido]propanoate (1200443-27-1)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 25 ℃; for 2h; Inert atmosphere;

DOI:10.1055/s-0029-1216937

upstream raw materials:

[4-methoxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-acetic acid methyl ester

(3-bromo-4-methoxy-phenyl)-acetic acid

bis(pinacol)diborane

Downstream raw materials:

methyl (S)-3-(4-hydroxyphenyl)-2-[(R)-2-{2-[4-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetamido}-2-phenylacetamido]propanoate