anti-1-[N-(tert-butoxycarbonyl)amino]-3-benzyloxymethyl-1-cyclobutane-1-carboxylic acid

Base Information

• Chemical Name: anti-1-[N-(tert-butoxycarbonyl)amino]-3-benzyloxymethyl-1-cyclobutane-1-carboxylic acid
• CAS No.: 439090-02-5
• Molecular Formula: C₁₈H₂₅NO₅
• Molecular Weight: 335.4
• Mol file: 439090-02-5.mol

Synonyms:anti-1-[N-(tert-butoxycarbonyl)amino]-3-benzyloxymethyl-1-cyclobutane-1-carboxylic acid

Chemical Property of anti-1-[N-(tert-butoxycarbonyl)amino]-3-benzyloxymethyl-1-cyclobutane-1-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of anti-1-[N-(tert-butoxycarbonyl)amino]-3-benzyloxymethyl-1-cyclobutane-1-carboxylic acid

There total 4 articles about anti-1-[N-(tert-butoxycarbonyl)amino]-3-benzyloxymethyl-1-cyclobutane-1-carboxylic 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:

di-tert-butyl dicarbonate (24424-99-5) + 1-amino-3-benzyloxymethyl-cyclobutanecarboxylic acid → anti-1-[N-(tert-butoxycarbonyl)amino]-3-benzyloxymethyl-1-cyclobutane-1-carboxylic acid (439090-02-5)

Guidance literature:

DOI:10.1002/jlcr.466

Reference yield:

3-benzyloxymethyl-cyclobutanone (172324-67-3) → anti-1-[N-(tert-butoxycarbonyl)amino]-3-benzyloxymethyl-1-cyclobutane-1-carboxylic acid (439090-02-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 16 percent / aq. (NH₄)2CO₃; aq. NH₄Cl / ethanol / 72 h / 60 °C

2: aq. NaOH / 12 h / 120 °C

3: Et₃N / methanol / 12 h / 20 °C

With sodium hydroxide; ammonium carbonate; ammonium chloride; triethylamine; In methanol; ethanol;

DOI:10.1021/jm010242p

Reference yield:

anti-2-[(benzyloxy)methyl]-5,7-diazaspiro[3.4]octane-6,8-dione (439090-00-3) → anti-1-[N-(tert-butoxycarbonyl)amino]-3-benzyloxymethyl-1-cyclobutane-1-carboxylic acid (439090-02-5)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. NaOH / 12 h / 120 °C

2: Et₃N / methanol / 12 h / 20 °C

With sodium hydroxide; triethylamine; In methanol;

DOI:10.1021/jm010242p

upstream raw materials:

di-tert-butyl dicarbonate

3-benzyloxymethyl-cyclobutanone

anti-2-[(benzyloxy)methyl]-5,7-diazaspiro[3.4]octane-6,8-dione

3-(benzyloxymethyl)-2,2-dichlorocyclobutanone

Downstream raw materials:

anti-1-[N-(tert-butoxycarbonyl)amino]-3-benzyloxymethyl-1-cyclobutane-1-carboxylic acid t-butyl ester

trans-1-amino-3-fluoromethylcyclobutane-1-carboxylic acid

Refernces

• 1、 Martarello, Laurent,McConathy, Jonathan,Camp, Mel,Malveaux, Eugene,Olson, Jeffrey,Bowers, Geoffrey,Goodman, Mark M.. "Synthesis and Biological Evaluation of Syn and Anti FMACBC, New Amino Acids for Tumor Imaging With PET". . p. S385 - S387. Retrieved 2007/10/03.