Methyl 3-(4-methoxyphenyl)oxirane-2-carboxylate

Base Information

• Chemical Name: Methyl 3-(4-methoxyphenyl)oxirane-2-carboxylate
• CAS No.: 42245-42-1
• Molecular Formula: C11H12O4
• Molecular Weight: 208.214
• European Community (EC) Number: 404-130-2,255-735-1
• DSSTox Substance ID: DTXSID90885863
• Nikkaji Number: J241.507K
• Mol file: 42245-42-1.mol

Synonyms:3-(-methoxyphenyl)glycidic acid methylester;methyl (2R,3S)-3-(4-methoxyphenyl)glycidate;methyl 2,3-epoxy-3-(4-methoxyphenyl)propionate;methyl 3-(4-methoxyphenyl)glycidate;methyl-3-(4-methoxyphenyl)glycidate;t-methyl-3-phenylglycidate

Chemical Property of Methyl 3-(4-methoxyphenyl)oxirane-2-carboxylate

Chemical Property:

• Vapor Pressure: 0.00133mmHg at 25°C
• Melting Point: 69-71 °C(lit.)
• Refractive Index: 1.534
• Boiling Point: 297.7 °C at 760 mmHg
• Flash Point: 129.2 °C
• PSA: 48.06000
• Density: 1.224 g/cm³
• LogP: 1.30810
• Solubility.: Dichloromethane; Chloroform; Ethyl Acetate; DMSO
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 208.07355886
• Heavy Atom Count: 15
• Complexity: 233

Purity/Quality:

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

Methyl trans-3-(4-methoxyphenyl)glycidate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)C2C(O2)C(=O)OC
• General Description: Methyl 3-(4-methoxyphenyl)oxirane-2-carboxylate (also known as methyl trans-(±)-3-(4-methoxyphenyl) glycidate) is a glycidate ester that can be enantioselectively resolved using crude Mung bean epoxide hydrolase immobilized in a gelatin matrix. The enzymatic process yields the (2S,3R)-enantiomer with high enantiomeric excess (ee >99%) and near-quantitative yield, demonstrating its utility as a key intermediate in the synthesis of enantiomerically pure compounds for pharmaceutical applications.

Technology Process of Methyl 3-(4-methoxyphenyl)oxirane-2-carboxylate

There total 13 articles about Methyl 3-(4-methoxyphenyl)oxirane-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: 95.0%

methyl (2-RS,3-SR)-3-hydroxy-3-(4-methoxyphenyl)-2-<(4-methoxyphenyl)sulfonyloxy>propanoate → methyl (2-RS,3-SR)-2,3-epoxy-3-(4-methoxyphenyl)propanoate (42245-42-1,84056-02-0,84976-49-8,88877-35-4,96125-49-4,105560-93-8,126060-70-6,134931-64-9,137173-40-1)

Guidance literature:

With N-benzyl-trimethylammonium hydroxide; In tetrahydrofuran; methanol; for 1h; Ambient temperature;

Reference yield: 88.4%

4-methoxy-benzaldehyde (123-11-5) + methyl chloroacetate (96-34-4) → methyl 3-(4-methoxyphenyl)glycidate (42245-42-1)

Guidance literature:

With sodium methylate; In ethanol; at 5 - 35 ℃; for 2h;

Reference yield: 17.1%

4-methoxy-benzaldehyde (123-11-5) + methyl chloroacetate (96-34-4) → methyl trans-3-(4-methoxyphenyl)glycidate (96125-49-4) + methyl (2-RS,3-SR)-2,3-epoxy-3-(4-methoxyphenyl)propanoate (42245-42-1,84056-02-0,84976-49-8,88877-35-4,96125-49-4,105560-93-8,126060-70-6,134931-64-9,137173-40-1)

Guidance literature:

With sodium hydride; In N,N,N,N,N,N-hexamethylphosphoric triamide; Ambient temperature;

upstream raw materials:

4-methoxy-benzaldehyde

methyl chloroacetate

3-(4-methoxy-phenyl)acrylic acid methyl ester

3-chloro-benzenecarboperoxoic acid

Downstream raw materials:

2-Hydroxy-3-(4-methoxy-phenyl)-3-(2-methylamino-phenylsulfanyl)-propionic acid methyl ester

3-[2-(2-Diethylamino-ethylamino)-phenylsulfanyl]-2-hydroxy-3-(4-methoxy-phenyl)-propionic acid methyl ester

threo-2-hydroxy-3-<(2-amino-5-methoxyphenyl)thio>-3-(4-methoxyphenyl)propionic acid methyl ester

4-Methoxyphenylacetaldehyde

Refernces

Gelozymes in organic synthesis. Part IV: Resolution of glycidate esters with crude Mung bean (Phaseolus radiatus) epoxide hydrolase immobilized in gelatin matrix

10.1016/j.tetasy.2008.01.036

The research focuses on the use of crude Mung bean (Phaseolus radiatus) epoxide hydrolase immobilized in a gelatin matrix for the stereoselective resolution of glycidate esters, specifically ethyl trans-(±)-3-phenyl glycidate (1a) and methyl trans-(±)-3-(4-methoxyphenyl) glycidate (1b). The experiments involved the immobilization of the enzyme in a gelatin gel, which was then used to selectively open the epoxide ring of the glycidate esters, yielding (2S,3R)-glycidate esters with high enantiomeric excess (ee >99%) and good yields (45% for 1a and near quantitative for 1b). The reactions were carried out in diisopropyl ether, and the products were analyzed using chiral HPLC to determine their enantiomeric purity and configuration. The study also explored the effects of gelatin concentration and water content on enzyme stability and activity, optimizing these conditions for the best enzyme performance. The research demonstrated a sustainable and efficient method for the preparation of enantiomerically pure glycidate esters, which are important drug intermediates.