3'-hydroxymethyl-biphenyl-3-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: 3'-hydroxymethyl-biphenyl-3-carboxylic acid tert-butyl ester
• CAS No.: 901300-63-8
• Molecular Formula: C₁₈H₂₀O₃
• Molecular Weight: 284.355
• Mol file: 901300-63-8.mol

Synonyms:3'-hydroxymethyl-biphenyl-3-carboxylic acid tert-butyl ester

Chemical Property of 3'-hydroxymethyl-biphenyl-3-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3'-hydroxymethyl-biphenyl-3-carboxylic acid tert-butyl ester

There total 1 articles about 3'-hydroxymethyl-biphenyl-3-carboxylic acid tert-butyl 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: 95.0%

tert-butyl 3-bromobenzoate (69038-74-0) + [3-(hydroxymethyl)phenyl]boronic acid (87199-15-3) → 3'-hydroxymethyl-biphenyl-3-carboxylic acid tert-butyl ester (901300-63-8)

Guidance literature:

With sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 80 ℃; for 18h;

DOI:10.1055/s-2006-939059

Reference yield:

3'-hydroxymethyl-biphenyl-3-carboxylic acid tert-butyl ester (901300-63-8) → ((S)-20-Methyl-9,16-dioxo-8,15-diaza-tricyclo[15.3.1.12,6]docosa-1(20),2,4,6(22),17(21),18-hexaen-10-yl)-carbamic acid benzyl ester

Guidance literature:

Multi-step reaction with 7 steps

1: triethylamine / dichloromethane / 1 h / 0 - 20 °C

2: sodium azide / N,N-dimethyl-formamide / 20 °C

3: triphenylphosphine / tetrahydrofuran; water / 4 h / 70 °C

4: dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide / dichloromethane / 18 h / 20 °C

5: trifluoroacetic acid / water / 18 h / 20 °C

6: dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide / dichloromethane / 16 h / 20 °C

7: 1,4-diaza-bicyclo[2.2.2]octane / tetrahydrofuran / 18 h / 70 °C

With 1,4-diaza-bicyclo[2.2.2]octane; dmap; sodium azide; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; 7: Staudinger Ligation reaction;

DOI:10.1055/s-2006-939059

Reference yield:

3'-hydroxymethyl-biphenyl-3-carboxylic acid tert-butyl ester (901300-63-8) → 3'-[((S)-6-Azido-2-benzyloxycarbonylamino-hexanoylamino)-methyl]-biphenyl-3-carboxylic acid

Guidance literature:

Multi-step reaction with 5 steps

1: triethylamine / dichloromethane / 1 h / 0 - 20 °C

2: sodium azide / N,N-dimethyl-formamide / 20 °C

3: triphenylphosphine / tetrahydrofuran; water / 4 h / 70 °C

4: dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide / dichloromethane / 18 h / 20 °C

5: trifluoroacetic acid / water / 18 h / 20 °C

With dmap; sodium azide; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1055/s-2006-939059

upstream raw materials:

tert-butyl 3-bromobenzoate

[3-(hydroxymethyl)phenyl]boronic acid

Downstream raw materials:

3'-Aminomethyl-biphenyl-3-carboxylic acid tert-butyl ester