158009-42-8

Basic information

• Product Name: 2-Aziridinecarboxylicacid,3-(1-methylethyl)-,methylester,(2S,3S)-(9CI)
• Synonyms: 2-Aziridinecarboxylicacid,3-(1-methylethyl)-,methylester,(2S,3S)-(9CI)
• CAS NO: 158009-42-8
• Molecular Formula: C7H13NO2
• Molecular Weight: 143.18
• Product Categories: CARBOXYLICESTER
• Mol File: 158009-42-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Aziridinecarboxylicacid,3-(1-methylethyl)-,methylester,(2S,3S)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Aziridinecarboxylicacid,3-(1-methylethyl)-,methylester,(2S,3S)-(9CI)(158009-42-8)
• EPA Substance Registry System: 2-Aziridinecarboxylicacid,3-(1-methylethyl)-,methylester,(2S,3S)-(9CI)(158009-42-8)

Safety Data

• Hazardous Substances Data: 158009-42-8(Hazardous Substances Data)

Usage

General Description

2-Aziridinecarboxylicacid, 3-(1-methylethyl)-, methylester, (2S,3S)-(9CI) is a chemical compound with the molecular formula C7H11NO2. It is also known by its IUPAC name, (2S,3S)-3-isopropyl-2-aziridinecarboxylic acid methyl ester. 2-Aziridinecarboxylicacid,3-(1-methylethyl)-,methylester,(2S,3S)-(9CI) is a derivative of aziridine, which is a highly reactive and versatile three-membered heterocyclic ring containing one nitrogen atom. It is commonly used in organic synthesis as a building block for the preparation of various compounds. Additionally, it has potential applications in the pharmaceutical industry as a precursor for the synthesis of pharmaceutical drugs. However, it is important to handle 2-Aziridinecarboxylicacid,3-(1-methylethyl)-,methylester,(2S,3S)-(9CI) with caution as aziridine derivatives are known to be toxic and potentially harmful to human health.

Relevant articles and documents

Aza-Darzens asymmetric synthesis of N-(p-toluenesulfinyl)aziridine 2- carboxylate esters from sulfinimines (N-sulfinyl imines)

The one-step aza-Darzens reaction of sulfinimines 2 with lithium α- bromoenolates readily affords diversely substituted cis and trans N- sulfinylaziridine 2-carboxylate esters 3 and 7 in good yield and excellent diastereoselectivity. Higher yields, but lower de's, result when a mixture of the α-bromo ester and 2 are treated with base. The N-sulfinyl group is transformed, nearly quantitatively, without ring opening, into the N-tosyl activating group by oxidation with m-CPBA. Selective removal of the N- sulfinyl group in aziridines 3a and 3h with TFA/H2O affords 1H-aziridines 21 which are difficult to prepared by other means. However, C(3) activated azirines such as 3b undergo ring-opening under these conditions. Alternatively, the N-sulfinyl group, even in C(3)-activated aziridines, was selectively and efficiently removed by treatment of the aziridine with 2 equiv of MeMgBr.

Aziridine compounds, methods of preparation and reactions thereof

Novel N-sulfinyl-2-carboxyaziridine compounds and novel N-hydrogen-2-hydroxymethylaziridine compounds are provided. The asymmetric synthesis of N-sulfinylaziridines is readily accomplished in high diastereomeric purity and good yield by the Darzens-type reaction of the metal enolate of an α-haloester and an enantiopure sulfinimine. Ring-opening of these aziridines affords α-amino acids and the otherwise difficult to prepare syn-β-hydroxy-α-amino acids, both key structural units found in many bioactive materials. The N-sulfinyl radical may be selectively removed from the novel aziridine compounds by treatment with acid or base. Alternatively, the N-sulfinyl radical may be oxidized to provide the corresponding N-sulfonyl-aziridine, or reduced to form the corresponding 1H-2-hydroxymethylaziridine, either of which may subsequently be ring-opened to provide precursors to bioactive compounds.

Asymmetric synthesis using sulfinimines (thiooxime S-oxides)

The addition of diethylaluminum cyanide and the lithium enolate of methyl α-bromoacetate to sulfinimines (thiooxime S-oxides) is highly diastereoselective affording α-amino nitriles and N-sulfinylaziridines, respectively. Hydrolysis of the α-amino nitriles gives α-amino acids in high ee, while hydrolysis of N-sulfinylaziridine carboxylic acids give β-hydroxy-α-amino acids. The latter compounds were transformed into (+)-thiamphenicol, a broad spectrum antibiotic and sphingosine, an important component of the sphingolipids.

Asymmetric Synthesis and Reactions of cis-N-(p-Toluenesulfinyl)aziridine-2-carboxylic Acids

cis-Aziridine-2-carboxylic acids, 2, precursors of the difficult to prepare syn-β-hydroxy-α-amino acid structural unit, are prepared in high diastereomeric purity by a Darzens-type reaction of the lithium enolate of methyl bromoacetate with enantiopure sulfinimines 1.