(2S-trans)-4-Azido-1,2-pyrrolidinedicarboxylic Acid 1-(1,1-DiMethylethyl) 2-Methyl Ester

Base Information

• Chemical Name: (2S-trans)-4-Azido-1,2-pyrrolidinedicarboxylic Acid 1-(1,1-DiMethylethyl) 2-Methyl Ester
• CAS No.: 121147-97-5
• Molecular Formula: C11H18 N4 O4
• Molecular Weight: 270.288
• Mol file: 121147-97-5.mol

Synonyms:1,2-Pyrrolidinedicarboxylicacid, 4-azido-, 1-(1,1-dimethylethyl) 2-methyl ester, (2S-trans)-

Chemical Property of (2S-trans)-4-Azido-1,2-pyrrolidinedicarboxylic Acid 1-(1,1-DiMethylethyl) 2-Methyl Ester

Chemical Property:

• PSA: 105.59000
• LogP: 1.23836
• Storage Temp.: -20°C Freezer
• Solubility.: CDCl3, CD3OD

Purity/Quality:

99% ^*data from raw suppliers

(2S,4R)-4-Azido-1,2-pyrrolidinedicarboxylicAcid1-(1,1-Dimethylethyl)2-MethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (2S-trans)-4-Azido-1,2-pyrrolidinedicarboxylic Acid 1-(1,1-DiMethylethyl) 2-Methyl Ester is used in the preparation of neuronal nitric oxide synthase inhibitors.

Technology Process of (2S-trans)-4-Azido-1,2-pyrrolidinedicarboxylic Acid 1-(1,1-DiMethylethyl) 2-Methyl Ester

There total 23 articles about (2S-trans)-4-Azido-1,2-pyrrolidinedicarboxylic Acid 1-(1,1-DiMethylethyl) 2-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: 98.0%

(2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester (74844-91-0,114676-69-6,135042-17-0,227935-38-8,102195-79-9) → 1-tert-butyl 2-methyl (2S,4R)-4-azido-1,2-pyrrolidinedicarboxylate (121147-97-5)

Guidance literature:

With diphenyl-phosphinic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran;

DOI:10.1021/ol0161054

Reference yield: 95.0%

(2S,4S)-2-methyl N-Boc-4-((methylsulfonyl)oxy)pyrrolidine-2-carboxylate (121147-93-1) → 1-tert-butyl 2-methyl (2S,4R)-4-azido-1,2-pyrrolidinedicarboxylate (121147-97-5)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 0 - 80 ℃; for 4h;

Reference yield: 95.0%

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate (74844-91-0) → 1-tert-butyl 2-methyl (2S,4R)-4-azido-1,2-pyrrolidinedicarboxylate (121147-97-5)

Guidance literature:

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate; With methanesulfonic acid; triethylamine; triphenylphosphine; di-isopropyl azodicarboxylate; In toluene; at 70 ℃; for 3h;

With sodium azide; In N,N-dimethyl-formamide; at 80 ℃;

DOI:10.1021/ja067148o

upstream raw materials:

O2-methyl O1-tert-butyl (2S,4S)-4-(p-tolylsulfonyloxy)pyrrolidine-1,2-dicarboxylic acid

(2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester

(2S,4S)-2-methyl N-Boc-4-((methylsulfonyl)oxy)pyrrolidine-2-carboxylate

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

Downstream raw materials:

tert-butyl (2S,4R)-2-formyl-4-((phenylsulfonyl)amino)-pyrrolidine-1-carboxylate

tert-butyl (2S,4R)-2-formyl-4-(((4-methylphenyl)sulfonyl)amino)pyrrolidine-1-carboxylate

tert-butyl (2S,4R)-2-formyl-4-(((4-chlorophenyl)sulfonyl)amino)pyrrolidine-1-carboxylate

tert-butyl (2S,4R)-2-formyl-4-(((4-methoxyphenyl)sulfonyl)amino)pyrrolidine-1-carboxylate

Refernces

• 1、 Kuemin, Michael,Sonntag, Louis-Sebastian,Wennemers, Helma. "Azidoproline containing helices: Stabilization of the polyproline II structure by a functionalizable group". . p. 466 - 467. Retrieved 2007.
• 2、 Braun, Alexandra,Gallo, Francesca,Hambira, Chido M.,Hechler, Torsten,Kato, Brandon,Müller, Christoph,Matinkhoo, Kaveh,Pahl, Andreas,Perrin, David M.,Wei, Charlie,Wong, Antonio A. W. L.. "Design, Synthesis, and Biochemical Evaluation of Alpha-Amanitin Derivatives Containing Analogs of the trans-Hydroxyproline Residue for Potential Use in Antibody-Drug Conjugates". . p. 10282 - 10292. Retrieved 2021/06/25.
• 3、 Bonneure, Eli,De Baets, Amber,De Decker, Sam,Van den Berge, Koen,Clement, Lieven,Vyverman, Wim,Mangelinckx, Sven. "Altering the sex pheromone cyclo(L-pro-l-pro) of the diatom seminavis robusta towards a chemical probe". . p. 1 - 14. Retrieved 2021/01/26.