6-((tert-butoxycarbonylamino)methyl)picolinic acid

Base Information

• Chemical Name: 6-((tert-butoxycarbonylamino)methyl)picolinic acid
• CAS No.: 171670-07-8
• Molecular Formula: C12H16N2O4
• Molecular Weight: 252.26600
• Mol file: 171670-07-8.mol

Synonyms:6-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]pyridine-2-carboxylic acid;6-{[(tertbutoxycarbonyl)amino]methyl}-2-pyridinecarboxylic acid;6-(tert-butoxycarbonylaminomethyl)pyridine 2-carboxylic acid;

Chemical Property of 6-((tert-butoxycarbonylamino)methyl)picolinic acid

Chemical Property:

• Melting Point: 238 - 240 °C
• Boiling Point: 446.1±40.0 °C(Predicted)
• PKA: 1.02±0.50(Predicted)
• PSA: 88.52000
• Density: 1.222±0.06 g/cm3(Predicted)
• LogP: 2.19540

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

6-(((Tert-Butoxycarbonyl)amino)methyl)picolinicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-((tert-butoxycarbonylamino)methyl)picolinic acid

There total 12 articles about 6-((tert-butoxycarbonylamino)methyl)picolinic 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: 88.0%

C13H18N2O4 → 6-{[(tertbutoxycarbonyl)amino]methyl}-2-pyridinecarboxylic acid (171670-07-8)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; at 25 ℃; for 1h;

DOI:10.1002/ejoc.201800855

Reference yield: 32.0%

ethyl 6-{[bis(tert-butoxycarbonyl)amino]methyl}pyridine-2-carboxylate (1258831-91-2) → 6-{[(tertbutoxycarbonyl)amino]methyl}-2-pyridinecarboxylic acid (171670-07-8) + 6-{[bis(tert-butoxycarbonyl)amino]methyl}pyridine-2-carboxylic acid (874619-36-0)

Guidance literature:

ethyl 6-{[bis(tert-butoxycarbonyl)amino]methyl}pyridine-2-carboxylate; With water; triethylamine; lithium bromide; In acetonitrile; at 20 ℃; for 24h;

With hydrogenchloride; water; In ethyl acetate; acetonitrile; pH=2 - 3;

DOI:10.1002/chem.201001861

Reference yield:

methyl 6-(hydroxymethyl)pyridine-2-carboxylate (39977-44-1) → 6-{[(tertbutoxycarbonyl)amino]methyl}-2-pyridinecarboxylic acid (171670-07-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: triphenylphosphine; carbon tetrabromide / N,N-dimethyl-formamide / 2 h / 25 °C / Inert atmosphere

1.2: 25 °C / Inert atmosphere

2.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 48 h / 25 °C / 3750.38 Torr

3.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 25 °C

With carbon tetrabromide; palladium 10% on activated carbon; hydrogen; triphenylphosphine; lithium hydroxide; In tetrahydrofuran; water; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.201800855

upstream raw materials:

ethyl 6-{[bis(tert-butoxycarbonyl)amino]methyl}pyridine-2-carboxylate

2,6-dimethylpyridine

6-methyl-2-pyridinecarboxylic acid

6-methylpicolinic acid methyl ester

Refernces

• 1、 -. "Polysubstituted pyridine medical intermediate and synthetic method thereof". . . Retrieved 2016/10/08.
• 2、 Irfan Ashiq, Muhammad,Tesfatsion, Biniam F.,Gaggini, Francesca,Dixon, Sally,Kilburn, Jeremy D.. "Dimeric self-assembly of pyridyl guanidinium carboxylates in polar solvents". experimental part. p. 12387 - 12397. Retrieved 2011/02/22.