4-[(2S)-OxiranylMethoxy]benzenepropanoic Acid Methyl Ester

Base Information

• Chemical Name: 4-[(2S)-OxiranylMethoxy]benzenepropanoic Acid Methyl Ester
• CAS No.: 112805-58-0
• Molecular Formula: C₁₃H₁₆O₄
• Molecular Weight: 236.268
• Mol file: 112805-58-0.mol

Synonyms:4-[(2S)-Oxiranylmethoxy]benzenepropanoic Acid Methyl Ester;

Chemical Property of 4-[(2S)-OxiranylMethoxy]benzenepropanoic Acid Methyl Ester

Chemical Property:

• PSA: 48.06000
• LogP: 1.56980

Purity/Quality:

97% ^*data from raw suppliers

4-[(2S)-Oxiranylmethoxy]benzenepropanoicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 4-[(2S)-Oxiranylmethoxy]benzenepropanoic Acid Methyl Ester is a chiral intermediate used for preparation of Esmolol hydrochloride optical isomers.

Technology Process of 4-[(2S)-OxiranylMethoxy]benzenepropanoic Acid Methyl Ester

There total 3 articles about 4-[(2S)-OxiranylMethoxy]benzenepropanoic Acid Methyl Ester 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: 46.0%

methyl 3-<4-(2,3-epoxypropoxy)phenyl>propionate (81147-94-6,246219-23-8) → methyl (S)-3-[4-(oxiran-2-ylmethoxy)phenyl]propanoate (112805-58-0,246219-23-8) + methyl (R)-3-[4-(2,3-dihydroxypropoxy)phenyl]propanoate

Guidance literature:

With (R,R)-(salen Co-(III)-OAc); water; at 0 - 20 ℃; for 8h; optical yield given as %ee; enantioselective reaction;

DOI:10.1080/00397911.2010.488495

Reference yield:

methyl 4-hydroxycinnamate (3943-97-3) → methyl (S)-3-[4-(oxiran-2-ylmethoxy)phenyl]propanoate (112805-58-0,246219-23-8) + methyl (R)-3-[4-(2,3-dihydroxypropoxy)phenyl]propanoate

Guidance literature:

Multi-step reaction with 3 steps

1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 12 h / 20 °C

2: potassium carbonate / acetonitrile / 6 h / Reflux

3: (R,R)-(salen Co-(III)-OAc); water / 8 h / 0 - 20 °C

With palladium 10% on activated carbon; (R,R)-(salen Co-(III)-OAc); water; hydrogen; potassium carbonate; In ethyl acetate; acetonitrile;

DOI:10.1080/00397911.2010.488495

Reference yield:

4-hydroxy-benzaldehyde (123-08-0,65581-83-1) → methyl (S)-3-[4-(oxiran-2-ylmethoxy)phenyl]propanoate (112805-58-0,246219-23-8) + methyl (R)-3-[4-(2,3-dihydroxypropoxy)phenyl]propanoate

Guidance literature:

Multi-step reaction with 4 steps

1: dichloromethane / 6 h / 20 °C

2: palladium 10% on activated carbon; hydrogen / ethyl acetate / 12 h / 20 °C

3: potassium carbonate / acetonitrile / 6 h / Reflux

4: (R,R)-(salen Co-(III)-OAc); water / 8 h / 0 - 20 °C

With palladium 10% on activated carbon; (R,R)-(salen Co-(III)-OAc); water; hydrogen; potassium carbonate; In dichloromethane; ethyl acetate; acetonitrile; 1: Wittig reaction;

DOI:10.1080/00397911.2010.488495

upstream raw materials:

methyl 4-hydroxycinnamate

4-hydroxy-benzaldehyde

methyl 3-<4-(2,3-epoxypropoxy)phenyl>propionate

Downstream raw materials:

methyl (S)-3-[4-[2-Hydroxy-3-(isopropylamino)propoxy]phenyl]propanoate

Refernces