(S)-tert-butyl methyl aziridine-1,2-dicarboxylate

Base Information

• Chemical Name: (S)-tert-butyl methyl aziridine-1,2-dicarboxylate
• CAS No.: 126496-79-5
• Molecular Formula: C9H15 N O4
• Molecular Weight: 201.222
• Hs Code.: 2933990090
• Mol file: 126496-79-5.mol

Synonyms:1,2-Aziridinedicarboxylicacid, 1-(1,1-dimethylethyl) 2-methyl ester, (S)-

Chemical Property of (S)-tert-butyl methyl aziridine-1,2-dicarboxylate

Chemical Property:

• Boiling Point: 249 ºC
• PKA: -5.60±0.40(Predicted)
• Flash Point: 104 ºC
• PSA: 55.61000
• Density: 1.189
• LogP: 0.71660
• Storage Temp.: 2-8°C

Purity/Quality:

99% ^*data from raw suppliers

1-tert-butyl2-methyl(2S)-aziridine-1,2-dicarboxylate 97.0% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (S)-tert-butyl methyl aziridine-1,2-dicarboxylate

There total 4 articles about (S)-tert-butyl methyl aziridine-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: 89.0%

di-tert-butyl dicarbonate (24424-99-5) + methyl (2S)-N-tritylaziridine-2-carboxylate (75154-68-6) → (S)-N-tert-butoxycarbonyl aziridine-2-carboxylate methyl ester (126496-79-5)

Guidance literature:

methyl (2S)-N-tritylaziridine-2-carboxylate; With trifluoroacetic acid; In methanol; dichloromethane; at -30 - 0 ℃; Inert atmosphere;

di-tert-butyl dicarbonate; With triethylamine; In acetonitrile; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/ol9024919

Reference yield: 73.0%

di-tert-butyl dicarbonate (24424-99-5) + (S)-methyl aziridine-2-carboxylate (75154-69-7) → (S)-N-tert-butoxycarbonyl aziridine-2-carboxylate methyl ester (126496-79-5)

Guidance literature:

With dmap; triethylamine; for 12h;

DOI:10.1016/0040-4039(96)00676-4

Reference yield:

tert-butyl carbazate (4248-19-5) → (S)-N-tert-butoxycarbonyl aziridine-2-carboxylate methyl ester (126496-79-5)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium carbonate; sodium hypochlorite pentahydrate; N-benzyl-N,N,N-triethylammonium chloride / acetonitrile / 3 h / 20 °C

2: dichloromethane / 80 h / -40 °C

3: dmap / 5 h / 20 °C

With dmap; sodium hypochlorite pentahydrate; N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate; In dichloromethane; acetonitrile;

DOI:10.1039/d1ra04297a

upstream raw materials:

di-tert-butyl dicarbonate

methyl (2S)-N-tritylaziridine-2-carboxylate

(S)-methyl aziridine-2-carboxylate

methanol

Downstream raw materials:

di-tert-butyl (S)-aziridine-1,2-dicarboxylate

(S)-4-methoxycarbonyl-oxazolidin-2-one

methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(1H-indol-3-yl)propanoate

Refernces

• 1、 -. "MACROCYCLIC COMPOUNDS AS PROTEASOME INHIBITORS". Paragraph 0417. . Retrieved 2019/05/02.
• 2、 Wu, Yan-Chao,Zhu, Jieping. "Asymmetrie total syntheses of (-)-renieramycin M and G and (-)-jorumycin using aziridine as a lynchpin". supporting information; experimental part. p. 5558 - 5561. Retrieved 2010/02/28.