TERT-BUTYL 2-OXOAZETIDINE-1-CARBOXYLATE

Base Information

• Chemical Name: TERT-BUTYL 2-OXOAZETIDINE-1-CARBOXYLATE
• CAS No.: 1140510-99-1
• Molecular Formula: C8H13NO3
• Molecular Weight: 171.196
• Hs Code.: 2933790090
• Mol file: 1140510-99-1.mol

Synonyms:1,1-Dimethylethyl 2-oxoazetidine-1-carboxylate;1-(tert-Butoxycarbonyl)-4-oxoazetidine;2-Oxoazetidine-1-carboxylic acid tert-butyl ester;

Chemical Property of TERT-BUTYL 2-OXOAZETIDINE-1-CARBOXYLATE

Chemical Property:

• Boiling Point: 285.5±9.0 °C(Predicted)
• PKA: -2.36±0.20(Predicted)
• PSA: 46.61000
• Density: 1.174±0.06 g/cm3(Predicted)
• LogP: 1.09170
• Storage Temp.: 2-8°C

Purity/Quality:

NLT 98% ^*data from raw suppliers

tert-Butyl2-Oxoazetidine-1-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: tert-Butyl 2-Oxoazetidine-1-carboxylate can be used in the preparation of N-tosyl and N-(alkoxycarbonyl) β-lactams as reagents for the chemoselective labeling of the phosphopantetheine thiol group of acyl carrier proteins. It can also be used in the preparation of indolyl azetidine rMCHR1 antagonists.

Technology Process of TERT-BUTYL 2-OXOAZETIDINE-1-CARBOXYLATE

There total 1 articles about TERT-BUTYL 2-OXOAZETIDINE-1-CARBOXYLATE 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: 93.0%

2-azetidinone (930-21-2) + di-tert-butyl dicarbonate (24424-99-5) → tert-butyl 2-oxoazetidine-1-carboxylate (1140510-99-1)

Guidance literature:

With dmap; In acetonitrile; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/acs.orglett.9b02887

Reference yield: 99.0%

tert-butyl 2-oxoazetidine-1-carboxylate (1140510-99-1) → N-tert-butoxycarbonyl-3-aminopropanol (58885-58-8)

Guidance literature:

With Cp*RuCl{(C6H5)2P-(CH2)2NH2-κ2-P,N}; potassium tert-butylate; hydrogen; In tert-butyl alcohol; at 80 ℃; for 24h; under 22502.3 Torr; Autoclave;

DOI:10.1002/anie.200805307

Reference yield: 56.7%

tert-butyl 2-oxoazetidine-1-carboxylate (1140510-99-1) + L-phenylalanine tert-butyl ester (16874-17-2) → N-Boc-β-alanyl-L-phenylalanine t-butyl ester (1190306-74-1)

Guidance literature:

With Burkholderia cepacia lipase PS-D; In di-isopropyl ether; at 37 ℃; for 6h; Enzymatic reaction;

DOI:10.1016/j.tetasy.2009.05.040

upstream raw materials:

2-azetidinone

di-tert-butyl dicarbonate

Downstream raw materials:

N-tert-butoxycarbonyl-3-aminopropanol

N-Boc-β-alanyl-L-phenylalanine t-butyl ester

N-Boc-β-alanyl-D-phenylalanine t-butyl ester

3-oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester

Refernces

• 1、 Duchemin, Nicolas,Buccafusca, Roberto,Daumas, Marc,Ferey, Vincent,Arseniyadis, Stellios. "A Unified Strategy for the Synthesis of Difluoromethyl- And Vinylfluoride-Containing Scaffolds". supporting information. p. 8205 - 8210. Retrieved 2019/10/16.
• 2、 Piperno, Anna,Carnovale, Caterina,Giofr, Salvatore V.,Iannazzo, Daniela. "Hydrozirconation of four-, five-, six- and seven-membered N-alkoxycarbonyl lactams to lactamols". supporting information; experimental part. p. 6880 - 6882. Retrieved 2012/02/05.