5-tert-Butoxycarbonylamino-pyridine-2-carboxylic acid methyl ester

Base Information

• Chemical Name: 5-tert-Butoxycarbonylamino-pyridine-2-carboxylic acid methyl ester
• CAS No.: 131052-40-9
• Molecular Formula: C₁₂H₁₆N₂O₄
• Molecular Weight: 252.27
• Mol file: 131052-40-9.mol

Synonyms:

Chemical Property of 5-tert-Butoxycarbonylamino-pyridine-2-carboxylic acid methyl ester

Chemical Property:

• Melting Point: 145-146 °C
• Boiling Point: 341.7±27.0 °C(Predicted)
• PKA: 12.36±0.70(Predicted)
• PSA: 77.52000
• Density: 1.203±0.06 g/cm3(Predicted)
• LogP: 2.28820

Purity/Quality:

98% ^*data from raw suppliers

Methyl 5-(tert-butoxycarbonylamino)picolinate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-tert-Butoxycarbonylamino-pyridine-2-carboxylic acid methyl ester

There total 4 articles about 5-tert-Butoxycarbonylamino-pyridine-2-carboxylic acid methyl 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: 93.2%

di-tert-butyl dicarbonate (24424-99-5) + methyl 5-amino-2-pyridinecarboxylate (67515-76-8) → methyl 5-[N-(tert-butoxycarbonyl)amino]-pyridine-2-carboxylate (131052-40-9)

Guidance literature:

With sodium hexamethyldisilazane; In N,N-dimethyl-formamide; at -40 - -30 ℃;

Reference yield: 55.0%

6-(methoxycarbonyl)nicotinic acid (17874-76-9) + tert-butyl alcohol (75-65-0) → methyl 5-[N-(tert-butoxycarbonyl)amino]-pyridine-2-carboxylate (131052-40-9)

Guidance literature:

With diphenylphosphoranyl azide; triethylamine; for 3.5h; Heating;

DOI:10.1021/jm00109a011

Reference yield:

5-amino-pyridine-2-carboxylic acid (24242-20-4,114849-40-0) → methyl 5-[N-(tert-butoxycarbonyl)amino]-pyridine-2-carboxylate (131052-40-9)

Guidance literature:

Multi-step reaction with 2 steps

1: thionyl chloride / 96 h / 0 °C / Reflux

2: dmap / dichloromethane / 20 h / 20 °C / Inert atmosphere

With dmap; thionyl chloride; In dichloromethane;

upstream raw materials:

6-(methoxycarbonyl)nicotinic acid

tert-butyl alcohol

di-tert-butyl dicarbonate

methyl 5-amino-2-pyridinecarboxylate

Downstream raw materials:

(5-aminopyridin-2-yl)methanol

tert-butyl N-[6-(hydroxymethyl)pyridin-3-yl]carbamate

Refernces

• 1、 -. "Intermediate of (1S,4S)-2,5-diazabicyclo[2,2,2]octane derivative and preparation method of intermediate". Paragraph 0115; 0117; 0118. . Retrieved 2018/03/28.
• 2、 -. "PROBES FOR IMAGING HUNTINGTIN PROTEIN". Paragraph 0346. . Retrieved 2016/03/22.