1-tert-butyl 2-Methyl 4-azidopyrrolidine-1,2-dicarboxylate

Base Information

• Chemical Name: 1-tert-butyl 2-Methyl 4-azidopyrrolidine-1,2-dicarboxylate
• CAS No.: 84520-68-3
• Molecular Formula: C11H18N4O4
• Molecular Weight: 270.288
• Mol file: 84520-68-3.mol

Synonyms:(2S,4S)-1-Boc-4-azidopyrrolidine-2-carboxylic acid methylester;(2S,4S)-1-tert-butyl 2-methyl 4-azidopyrrolidine-1,2-dicarboxylate;

Chemical Property of 1-tert-butyl 2-Methyl 4-azidopyrrolidine-1,2-dicarboxylate

Chemical Property:

• PSA: 105.59000
• LogP: 1.23836

Purity/Quality:

97% ^*data from raw suppliers

Boc-L-cis-4-azidoprolineMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: Boc-L-cis-4-azidoproline Methyl Ester is used as a reagent for preparation of antibacterial and anti-TB tat-peptidomimetics with improved efficacy and half-life

Technology Process of 1-tert-butyl 2-Methyl 4-azidopyrrolidine-1,2-dicarboxylate

There total 2 articles about 1-tert-butyl 2-Methyl 4-azidopyrrolidine-1,2-dicarboxylate 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:

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate (74844-91-0) → N-tert-butoxycarbonyl-cis-4-azido-L-proline methyl ester (84520-68-3) + 1-tert-butyl 2-methyl (2S,4S)-4-fluoropyrrolidine-1,2-dicarboxylate (203866-16-4)

Guidance literature:

With sodium azide; fluorosulfonyl fluoride; tetrabutylammoniun azide; triethylamine; In acetonitrile; for 1h; Product distribution / selectivity; cooling with ice;

Reference yield:

L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) → N-tert-butoxycarbonyl-cis-4-azido-L-proline methyl ester (84520-68-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 53.4 g / triethylamine / CH₂Cl₂ / 4 h / 0 - 5 °C

2: 56.2 g / triethylamine / CH₂Cl₂ / 3 h / 0 - 5 °C

3: 100 percent / sodium azide / dimethylsulfoxide / 90 °C

With sodium azide; triethylamine; In dichloromethane; dimethyl sulfoxide;

DOI:10.1016/S0968-0896(01)00397-2

Reference yield: 91.0%

N-tert-butoxycarbonyl-cis-4-azido-L-proline methyl ester (84520-68-3) + phenylacetylene (536-74-3) → N-(tert-butoxycarbonyl)-cis-4-(4-phenyl-1H-1,2,3-triazol-1-yl)-L-proline methyl ester (1186058-90-1)

Guidance literature:

With copper(l) iodide; N-ethyl-N,N-diisopropylamine; In methanol; at 20 ℃;

DOI:10.1016/j.bmcl.2009.06.006

upstream raw materials:

L-4-hydroxyproline methyl ester hydrochloride

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

Downstream raw materials:

(2S,4S)-4-aminopyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester hydrochloride

(2S,4S)-4-amino-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

(4S)-1-(tert-butoxycarbonyl)-4-azido-L-proline

N-Boc-(4S)-(benzamido)-L-proline methyl ester