(S)-benzyl 4-oxoazetidine-2-carboxylate

Base Information

• Chemical Name: (S)-benzyl 4-oxoazetidine-2-carboxylate
• CAS No.: 72776-05-7
• Molecular Formula: C11H11 N O3
• Molecular Weight: 205.213
• Hs Code.: 29337900
• DSSTox Substance ID: DTXSID50352046
• Nikkaji Number: J451.334G
• Wikidata: Q72440739
• Mol file: 72776-05-7.mol

Synonyms:72776-05-7;(S)-benzyl 4-oxoazetidine-2-carboxylate;(S)-Benzyl 2-azetidinone-4-carboxylate;benzyl (2S)-4-oxoazetidine-2-carboxylate;2-Azetidinecarboxylic acid, 4-oxo-, phenylmethyl ester, (2S)-;Benzyl (S)-4-oxo-2-azetidinecarboxylate;BENZYL (S)-4-OXOAZETIDINE-2-CARBOXYLATE;Benzyl (S)-(-)-4-oxo-2-azetidinecarboxylate;MFCD00798164;(S)-benzyl4-oxoazetidine-2-carboxylate;SCHEMBL6866934;DTXSID50352046;WGLLBHSIXLWVFU-VIFPVBQESA-N;AKOS000280692;AKOS005259568;AC-7731;FD15011;(s)-4-(benzyloxycarbonyl)-2-azetidinone;AS-64296;(S)-benzyl 4-oxo-2-azetidine-carboxylate;A9441;AM20041085;CS-0038817;AE-641/08488035;Benzyl (S)-(-)-4-oxo-2-azetidinecarboxylate, 97%

Chemical Property of (S)-benzyl 4-oxoazetidine-2-carboxylate

Chemical Property:

• Appearance/Colour: white to light yellow crystalline powder
• Vapor Pressure: 9.28E-07mmHg at 25°C
• Melting Point: 137-140 °C(lit.)
• Boiling Point: 404.7 °C at 760 mmHg
• PKA: 13.75±0.40(Predicted)
• Flash Point: 198.5 °C
• PSA: 55.40000
• Density: 1.268 g/cm³
• LogP: 0.94710
• Storage Temp.: 0-6°C
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 205.07389321
• Heavy Atom Count: 15
• Complexity: 259

Purity/Quality:

99% ^*data from raw suppliers

Benzyl(2S)-4-Oxoazetidine-2-carboxylate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1C(NC1=O)C(=O)OCC2=CC=CC=C2
• Isomeric SMILES: C1[C@H](NC1=O)C(=O)OCC2=CC=CC=C2
• Uses: Benzyl (S)-(-)-4-oxo-2-azetidinecarboxylate may be used in the preparation of its N-acetyl derivative, which can be a potential candidate as solid electrolyte interphase (SEI)-forming additive in lithium-ion batteries.

Technology Process of (S)-benzyl 4-oxoazetidine-2-carboxylate

There total 7 articles about (S)-benzyl 4-oxoazetidine-2-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: 47.0%

dibenzyl L-aspartate (2791-79-9) → (S)-benzyl 4-oxoazetidine-2-carboxylate (72776-05-7)

Guidance literature:

dibenzyl L-aspartate; With chloro-trimethyl-silane; triethylamine; In diethyl ether; at 0 ℃; for 1h;

With tert-butylmagnesium chloride; In diethyl ether; at -5 - 0 ℃; for 2h;

Reference yield:

(L)-N-(trimethylsilyl)dibenzyl aspartate (72776-06-8) → (S)-benzyl 4-oxoazetidine-2-carboxylate (72776-05-7)

Guidance literature:

With tert-butylmagnesium chloride; In diethyl ether; at 0 ℃; Yield given;

DOI:10.1016/S0040-4020(01)85592-7

Reference yield:

C16H21NO5 → (S)-benzyl 4-oxoazetidine-2-carboxylate (72776-05-7)

Guidance literature:

With cytochrome P₄₁₁ expressed in Escherichia coli; In aq. phosphate buffer; at 20 ℃; for 24h; pH=8; enantioselective reaction; Catalytic behavior; Enzymatic reaction;

DOI:10.1126/science.aaw9068

upstream raw materials:

dibenzyl L-aspartate

(L)-N-(trimethylsilyl)dibenzyl aspartate

D-aspartic acid dibenzyl ester

Downstream raw materials:

methyl (S)-(-)-2-oxoazetidine-4-carboxylate

benzyl (S)-4-oxo-1-(phenylcarbamoyl)azetidine-2-carboxylate

(R)-benzyl 1-(2,6-dimethylpyrimidin-4-yl)-4-oxoazetidine-2-carboxylate

C₂₄H₂₇N₃O₆

Refernces

• 1、 Cho, Inha,Jia, Zhi-Jun,Arnold, Frances H.. "RETRACTED ARTICLE: Site-selective enzymatic C-H amidation for synthesis of diverse lactams". . p. 575 - 578. Retrieved 2019/06/07.
• 2、 -. "Cyclic dipeptides and azetidinone compounds and their use in treating CNS injury and neurodegenerative disorders". Page/Page column 45. . Retrieved 2010/11/26.