(2S)-4-oxoazetidine-2-carboxylic acid

Base Information

• Chemical Name: (2S)-4-oxoazetidine-2-carboxylic acid
• CAS No.: 16404-94-7
• Molecular Formula: C4H5NO3
• Molecular Weight: 115.089
• Hs Code.: 2933790090
• European Community (EC) Number: 803-064-5
• DSSTox Substance ID: DTXSID80541628
• Nikkaji Number: J1.884.408G
• Wikidata: Q72498528
• Mol file: 16404-94-7.mol

Synonyms:16404-94-7;(S)-(-)-4-Oxo-2-azetidinecarboxylic acid;(2S)-4-oxoazetidine-2-carboxylic acid;(S)-4-Oxoazetidine-2-carboxylic acid;2-Azetidinecarboxylic acid, 4-oxo-, (2S)-;MFCD00799571;Pyroaspartic acid, L-;SCHEMBL690089;DTXSID80541628;(S)-4-Oxoazetidine-2-carboxylicacid;AKOS006237204;CS-W013626;(s)-4-oxo azetidine-2-carboxylic acid;(S)-4-oxo-azetidine-2-carboxylic acid;AS-80485;TS-01589;(s)-(-)-4-oxoazetidine-2-carboxylic acid;(S)-(?)-4-Oxo-2-azetidinecarboxylic acid;AM20080461;(S)-4-(-)-oxo-2-azetidinonecarboxilyc acid;EN300-103219;P10146;(S)-(-)-4-Oxo-2-azetidinecarboxylic acid, 98%;J-010109

Chemical Property of (2S)-4-oxoazetidine-2-carboxylic acid

Chemical Property:

• Vapor Pressure: 6.44E-11mmHg at 25°C
• Melting Point: 99-102 °C
• Refractive Index: 1.53
• Boiling Point: 489.4 °C at 760 mmHg
• PKA: 3.19±0.20(Predicted)
• Flash Point: 249.8 °C
• PSA: 66.40000
• Density: 1.519 g/cm³
• LogP: -0.71170
• Storage Temp.: 2-8°C
• XLogP3: -1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 115.026943022
• Heavy Atom Count: 8
• Complexity: 142

Purity/Quality:

98%,99%, ^*data from raw suppliers

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

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(NC1=O)C(=O)O
• Isomeric SMILES: C1[C@H](NC1=O)C(=O)O
• Uses: (S)-4-Oxoazetidine-2-carboxylic Acid, is a building block used for various chemical synthesis such as for the synthesis of NMDA receptor antagonists, 3-alkyl-L-aspartic acids, and orally active β-lactam inhibitors.

Technology Process of (2S)-4-oxoazetidine-2-carboxylic acid

There total 4 articles about (2S)-4-oxoazetidine-2-carboxylic acid 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: 98.0%

(S)-benzyl 4-oxoazetidine-2-carboxylate (72776-05-7) → (S)-4-oxo-azetidine-2-carboxylic acid (16404-94-7,62860-12-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; for 14h;

DOI:10.1016/0040-4020(95)00157-4

Reference yield: 95.0%

dibenzyl L-aspartate (2791-79-9) → (S)-4-oxo-azetidine-2-carboxylic acid (16404-94-7,62860-12-2)

Guidance literature:

dibenzyl L-aspartate; With chloro-trimethyl-silane; triethylamine;

With tert-butylmagnesium chloride;

With palladium on activated charcoal; hydrogen;

DOI:10.1021/jo402544p

Reference yield: 83.0%

methyl (S)-(-)-2-oxoazetidine-4-carboxylate (100188-44-1,111222-19-6) → (S)-4-oxo-azetidine-2-carboxylic acid (16404-94-7,62860-12-2)

Guidance literature:

With hydrogenchloride; for 4h; Heating;

DOI:10.3987/R-1986-09-2539

upstream raw materials:

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

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

dibenzyl L-aspartate

Downstream raw materials:

(S)-N-allyl-N-(benzyloxy)-4-oxoazetidine-2-carboxamide

thioacetic acid S-{(S)-6-[((S)-4-oxo-azetidine-2-carbonyl)-amino]-6-phenylcarbamoyl-hexyl} ester

(3S,6S,10aS)-6-((S)-2-(methylamino)propanamido)-5-oxo-N-(3-((S)-4-oxoazetidine-2-carboxamido)benzyl)decahydropyrrolo[1,2-a]azocine-3-carboxamide

(S)-1-(4-chlorophenyl)-4-oxoazetidine-2-carboxylic acid

Refernces

• 1、 Jobbins, Maria O.,Miller, Marvin J.. "Syntheses of hydroxamic acid-containing bicyclic β-lactams via palladium-catalyzed oxidative amidation of alkenes". . p. 1620 - 1625. Retrieved 2014/03/21.
• 2、 Baldwin, Jack E.,Adlington, Robert M.,Russell, Andrew T.,Smith, Marie L.. "Carbon based nucleophilic ring opening of activated monocyclic β-lactams; synthesis and stereochemical assignment of the ACE inhibitor WF-10129". . p. 4733 - 4762. Retrieved 2007/10/02.