Tert-butyl 2-(azidomethyl)-4-chlorobenzylcarbamate

Base Information

• Chemical Name: Tert-butyl 2-(azidomethyl)-4-chlorobenzylcarbamate
• CAS No.: 439117-41-6
• Molecular Formula: C13H17ClN4O2
• Molecular Weight: 296.757
• DSSTox Substance ID: DTXSID001133446
• Mol file: 439117-41-6.mol

Synonyms:tert-butyl 2-(azidomethyl)-4-chlorobenzylcarbamate;SCHEMBL15567657;JEQQUUZOGHHRJK-UHFFFAOYSA-N;DTXSID001133446;439117-41-6;1-azidomethyl-2-(tert-butyloxycarbonylaminomethyl)-5-chlorobenzene;Carbamic acid, [[2-(azidomethyl)-4-chlorophenyl]methyl]-, 1,1-dimethylethyl ester

Chemical Property of Tert-butyl 2-(azidomethyl)-4-chlorobenzylcarbamate

Chemical Property:

• XLogP3: 3.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 296.1040035
• Heavy Atom Count: 20
• Complexity: 377

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NCC1=C(C=C(C=C1)Cl)CN=[N+]=[N-]

Technology Process of Tert-butyl 2-(azidomethyl)-4-chlorobenzylcarbamate

There total 10 articles about Tert-butyl 2-(azidomethyl)-4-chlorobenzylcarbamate 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: 85.0%

→ 1-azidomethyl-2-(tert-butyloxycarbonylaminomethyl)-5-chlorobenzene (439117-41-6)

Guidance literature:

Reference yield:

tert-butyl 4-chloro-2-(hydroxymethyl)benzylcarbamate (439117-40-5) → 1-azidomethyl-2-(tert-butyloxycarbonylaminomethyl)-5-chlorobenzene (439117-41-6)

Guidance literature:

With diphenyl-phosphinic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 20 ℃; for 18h;

DOI:10.1016/S0960-894X(03)00732-7

Reference yield:

methyl-2-bromo-5-chlorobenzoate (27007-53-0) → 1-azidomethyl-2-(tert-butyloxycarbonylaminomethyl)-5-chlorobenzene (439117-41-6)

Guidance literature:

Multi-step reaction with 4 steps

1: Pd(PPh₃)4 / dimethylformamide / 60 °C

2: LiAlH₄ / tetrahydrofuran

3: tetrahydrofuran

4: DPPA / toluene

With lithium aluminium tetrahydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; diphenyl-phosphinic acid; In tetrahydrofuran; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.bmcl.2004.06.030

upstream raw materials:

tert-butyl 4-chloro-2-(hydroxymethyl)benzylcarbamate

di-tert-butyl dicarbonate

methyl-2-bromo-5-chlorobenzoate

[2-(aminomethyl)-5-chlorophenyl]methanol

Downstream raw materials:

2-(tert-butyloxycarbonylaminomethyl)-5-chlorobenzylamine

9-hydroxy-9-fluorenylcarbonyl-L-prolyl-2-(tert-butyloxycarbonylaminomethyl)-5-chlorobenzylamide

N-fluorenylmethoxycarbonyl-L-prolyl-2-(tert-butyloxycarbonylaminomethyl)-5-chlorobenzylamide

1-(N (fluorenylmethoxycarbonyl)-azetidin-2S-yl-carbonylaminomethyl)-2-(tert-butyloxycarbonylaminomethyl)-5-chlorobenzene