(S)-2-(2-nitro-benzenesulfonyl)-aziridine-2-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (S)-2-(2-nitro-benzenesulfonyl)-aziridine-2-carboxylic acid tert-butyl ester
• CAS No.: 389806-02-4
• Molecular Formula: C₁₃H₁₆N₂O₆S
• Molecular Weight: 328.346
• Mol file: 389806-02-4.mol

Synonyms:(S)-2-(2-nitro-benzenesulfonyl)-aziridine-2-carboxylic acid tert-butyl ester

Chemical Property of (S)-2-(2-nitro-benzenesulfonyl)-aziridine-2-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-(2-nitro-benzenesulfonyl)-aziridine-2-carboxylic acid tert-butyl ester

There total 5 articles about (S)-2-(2-nitro-benzenesulfonyl)-aziridine-2-carboxylic acid tert-butyl 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: 92.0%

N-(2-nitrobenzenesulfonyl)-L-serine tert-butyl ester (389806-01-3) → (S)-2-(2-nitro-benzenesulfonyl)-aziridine-2-carboxylic acid tert-butyl ester (389806-02-4)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at -5 ℃; for 1h;

DOI:10.1055/s-2001-18090

Reference yield: 50.0%

(2S)-1-(2-nitrobenzene-1-sulfonyl) aziridine-2-carboxylic acid (356519-34-1) + tert-butyl acetoacetate (1694-31-1) → (S)-2-(2-nitro-benzenesulfonyl)-aziridine-2-carboxylic acid tert-butyl ester (389806-02-4)

Guidance literature:

With sulfuric acid; at 20 ℃; for 24h; regioselective reaction;

DOI:10.1002/anie.201606657

Reference yield:

acetic acid tert-butyl ester (540-88-5) → (S)-2-(2-nitro-benzenesulfonyl)-aziridine-2-carboxylic acid tert-butyl ester (389806-02-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 65 percent / HClO₄

2: H₂; aq. HCl / Pd/C / dioxane / 16 h / 20 °C

3: aq. Na₂CO₃ / dioxane / 3 h / 20 °C

4: 92 percent / Ph₃P; DEAD / tetrahydrofuran / 1 h / -5 °C

With hydrogenchloride; perchloric acid; hydrogen; sodium carbonate; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; 3: Schotten-Baumann reaction / 4: Mitsunobu reaction;

DOI:10.1055/s-2001-18090

upstream raw materials:

N-(2-nitrobenzenesulfonyl)-L-serine tert-butyl ester

acetic acid tert-butyl ester

tert-butyl (2S)-2-amino-3-hydroxypropanoate

O-(phenylmethyl)-L-serine 1,1-dimethylethyl ester

Downstream raw materials:

(S)-2-[(S)-3-(2-nitro-benzenesulfonylamino)-2-oxoazetidin-1-yl]-propionic acid benzyl ester