2-(4-Biphenylyl)-2-(Boc-aMino)acetic Acid

Base Information

• Chemical Name: 2-(4-Biphenylyl)-2-(Boc-aMino)acetic Acid
• CAS No.: 369403-44-1
• Molecular Formula: C19H21NO4
• Molecular Weight: 327.38
• Hs Code.: 2924299090
• Mol file: 369403-44-1.mol

Synonyms:

Chemical Property of 2-(4-Biphenylyl)-2-(Boc-aMino)acetic Acid

Chemical Property:

• PSA: 79.12000
• LogP: 4.20840

Purity/Quality:

98.5% ^*data from raw suppliers

2-(4-Biphenylyl)-2-(Boc-amino)acetic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-(4-Biphenylyl)-2-(Boc-aMino)acetic Acid

There total 5 articles about 2-(4-Biphenylyl)-2-(Boc-aMino)acetic Acid 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:

2-amino-2-(4-bromophenyl)acetic acid (119397-06-7,71079-03-3) → 2-([1,1'-biphenyl]-4-yl)-2-((tert-butoxycarbonyl)amino)acetic acid (369403-44-1) + tert-butyl (1-([1,1'-biphenyl]-4-yl)-2-(hydroxyamino)-2-oxoethyl)carbamate

Guidance literature:

Multi-step reaction with 4 steps

1: sulfuric acid / Reflux

2: tetrahydrofuran; water / 20 °C

3: sodium carbonate; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran; water / 2 h / 100 °C / Microwave irradiation; Inert atmosphere; Sealed tube

4: hydroxylamine hydrochloride; sodium hydroxide / water; methanol / 20 °C

With bis-triphenylphosphine-palladium(II) chloride; sulfuric acid; hydroxylamine hydrochloride; sodium carbonate; sodium hydroxide; In tetrahydrofuran; methanol; water; 3: |Suzuki Coupling;

DOI:10.1016/j.ejmech.2016.01.015

Reference yield:

methyl 2-([1,1'-biphenyl]-4-yl)-2-((tert-butoxycarbonyl)amino)acetate → 2-([1,1'-biphenyl]-4-yl)-2-((tert-butoxycarbonyl)amino)acetic acid (369403-44-1) + tert-butyl (1-([1,1'-biphenyl]-4-yl)-2-(hydroxyamino)-2-oxoethyl)carbamate

Guidance literature:

With hydroxylamine hydrochloride; sodium hydroxide; In methanol; water; at 20 ℃;

DOI:10.1016/j.ejmech.2016.01.015

Reference yield:

2-(4-bromophenyl)-2-((tert-butoxycarbonyl)amino)acetic acid (917925-71-4,1228570-47-5) + phenylboronic acid (98-80-6) → 2-([1,1'-biphenyl]-4-yl)-2-((tert-butoxycarbonyl)amino)acetic acid (369403-44-1)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In tetrahydrofuran; at 90 ℃; for 8.05h; Time; Inert atmosphere; Microwave irradiation;

upstream raw materials:

2-amino-2-(4-bromophenyl)acetic acid

methyl 2-(4-bromophenyl)-2-((tert-butoxycarbonyl)amino)acetate

methyl 2-amino-2-(4-bromophenyl)acetate

2-(4-bromophenyl)-2-((tert-butoxycarbonyl)amino)acetic acid

Downstream raw materials:

2-([1,1’-biphenyl]-4-yl)glycine

Refernces

• 1、 Drinkwater, Nyssa,Vinh, Natalie B.,Mistry, Shailesh N.,Bamert, Rebecca S.,Ruggeri, Chiara,Holleran, John P.,Loganathan, Sasdekumar,Paiardini, Alessandro,Charman, Susan A.,Powell, Andrew K.,Avery, Vicky M.,McGowan, Sheena,Scammells, Peter J.. "Potent dual inhibitors of Plasmodium falciparum M1 and M17 aminopeptidases through optimization of S1 pocket interactions". . p. 43 - 64. Retrieved 2016/01/30.