trans-1-amino-3-(phenylsulfonyl)cyclobutane-1,3-dicarboxylic acid

Base Information

• Chemical Name: trans-1-amino-3-(phenylsulfonyl)cyclobutane-1,3-dicarboxylic acid
• CAS No.: 117488-22-9
• Molecular Formula: C₁₂H₁₃NO₆S
• Molecular Weight: 299.304
• Mol file: 117488-22-9.mol

Synonyms:trans-1-amino-3-(phenylsulfonyl)cyclobutane-1,3-dicarboxylic acid

Chemical Property of trans-1-amino-3-(phenylsulfonyl)cyclobutane-1,3-dicarboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of trans-1-amino-3-(phenylsulfonyl)cyclobutane-1,3-dicarboxylic acid

There total 6 articles about trans-1-amino-3-(phenylsulfonyl)cyclobutane-1,3-dicarboxylic 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: 85.0%

trans 1-azido-3-(phenylsulfonyl)cyclobutane-1,3-dicarboxylic acid (166666-96-2) → trans-1-amino-3-(phenylsulfonyl)cyclobutane-1,3-dicarboxylic acid (117488-22-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol;

DOI:10.1016/S0040-4039(00)80361-5

Reference yield:

3-Benzenesulfonyl-bicyclo[1.1.0]butane-1-carboxylic acid methyl ester (117487-81-7) → trans-1-amino-3-(phenylsulfonyl)cyclobutane-1,3-dicarboxylic acid (117488-22-9)

Guidance literature:

Multi-step reaction with 3 steps

1: tetramethylguanidinium azide / dimethylformamide / 85 °C

2: 1.) BuLi / 1.) THF, -78 deg C, 15 min, 2.) THF, from -78 deg C to RT

3: 81 percent / H₂ / 10percent Pd/C / ethanol / 20 h / 760 Torr / Ambient temperature

With n-butyllithium; hydrogen; tetramethylguanidinum azide; palladium on activated charcoal; In ethanol; N,N-dimethyl-formamide;

Reference yield:

1-azido-3-(phenylsulfonyl)cyclobutane-1-carboxylic acid → trans-1-amino-3-(phenylsulfonyl)cyclobutane-1,3-dicarboxylic acid (117488-22-9)

Guidance literature:

Multi-step reaction with 2 steps

2: 85 percent / hydrogen / Pd on C / ethanol

With hydrogen; palladium on activated charcoal; In ethanol;

DOI:10.1016/S0040-4039(00)80361-5

upstream raw materials:

trans 1-azido-3-(phenylsulfonyl)cyclobutane-1,3-dicarboxylic acid

3-Benzenesulfonyl-bicyclo[1.1.0]butane-1-carboxylic acid methyl ester

3-Benzenesulfonyl-bicyclo[1.1.0]butane-1-carboxylic acid

cis-1-Azido-3-(phenylsulfonyl)cyclobutane-1-carboxylic acid

Downstream raw materials:

Cis-ACBD

1-aminocyclobutane-cis-1,3-dicarboxylic acid

Refernces

• 1、 Gaoni, Yehiel. "REGIOSPECIFIC ADDITIONS OF HYDRAZOIC ACID AND BENZYLAMINE TO 1-(ARYLSULFONYL)BICYCLOBUTANES. APPLICATION TO THE SYNTHESIS OF CIS AND TRANS 2,7-METHANOGLUTAMIC ACIDS". . p. 1591 - 1594. Retrieved 2007/10/02.