methyl 4-[{(tert-butoxycarbonyl)amino}oxycarbonyl]benzoate

Base Information

• Chemical Name: methyl 4-[{(tert-butoxycarbonyl)amino}oxycarbonyl]benzoate
• CAS No.: 1613027-54-5
• Molecular Formula: C₁₄H₁₇NO₆
• Molecular Weight: 295.292
• Mol file: 1613027-54-5.mol

Synonyms:methyl 4-[{(tert-butoxycarbonyl)amino}oxycarbonyl]benzoate

Chemical Property of methyl 4-[{(tert-butoxycarbonyl)amino}oxycarbonyl]benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4-[{(tert-butoxycarbonyl)amino}oxycarbonyl]benzoate

There total 3 articles about methyl 4-[{(tert-butoxycarbonyl)amino}oxycarbonyl]benzoate 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: 83.0%

tert-Butyl N-hydroxycarbamate (36016-38-3) + 4-Methoxycarbonylbenzoyl chloride (7377-26-6) → methyl 4-[{(tert-butoxycarbonyl)amino}oxycarbonyl]benzoate (1613027-54-5)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 25 ℃; for 4h; Inert atmosphere;

DOI:10.1021/ol501338h

Reference yield:

tert-Butyl N-hydroxycarbamate (36016-38-3) + Monomethyl terephthalate (1679-64-7) → methyl 4-[{(tert-butoxycarbonyl)amino}oxycarbonyl]benzoate (1613027-54-5)

Guidance literature:

With dicyclohexyl-carbodiimide; In dichloromethane; at -15 ℃; for 0.5h; regioselective reaction; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.orglett.6b02724

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → methyl 4-[{(tert-butoxycarbonyl)amino}oxycarbonyl]benzoate (1613027-54-5)

Guidance literature:

Multi-step reaction with 2 steps

1: hydroxylamine hydrochloride; potassium carbonate / water; diethyl ether / 13 h / 20 °C / Inert atmosphere; Schlenk technique

2: dicyclohexyl-carbodiimide / dichloromethane / 0.5 h / -15 °C / Schlenk technique; Inert atmosphere

With hydroxylamine hydrochloride; potassium carbonate; dicyclohexyl-carbodiimide; In diethyl ether; dichloromethane; water;

DOI:10.1021/acs.orglett.6b02724

upstream raw materials:

tert-Butyl N-hydroxycarbamate

4-Methoxycarbonylbenzoyl chloride

Monomethyl terephthalate

di-tert-butyl dicarbonate

Downstream raw materials:

N-(tert-butyloxycarbonyl)-2-(pyridin-2-yl)aniline

tert-butyl [5-methyl-2-(pyridin-2-yl)phenyl]carbamate

tert-butyl [5-(benzyloxy)-2-(pyridin-2-yl)phenyl]carbamate

tert-butyl (4-methyl-2-(pyridin-2-yl)phenyl)carbamate