2-Azetidinepropanoic acid, 2-(Methoxycarbonyl)-1-(phenylMethyl)-, Methyl ester

Base Information

• Chemical Name: 2-Azetidinepropanoic acid, 2-(Methoxycarbonyl)-1-(phenylMethyl)-, Methyl ester
• CAS No.: 1353160-88-9
• Molecular Formula: C₁₆H₂₁NO₄
• Molecular Weight: 291.347
• Hs Code.: 2933998090
• Mol file: 1353160-88-9.mol

Synonyms:2-Azetidinepropanoic acid, 2-(Methoxycarbonyl)-1-(phenylMethyl)-, Methyl ester;methyl 1-benzyl-2-(3-methoxy-3-oxopropyl)azetidine-2-carboxylate;2-(Methoxycarbonyl)-1-(phenylmethyl)-2-azetidinepropanoicacid,methylester

Chemical Property of 2-Azetidinepropanoic acid, 2-(Methoxycarbonyl)-1-(phenylMethyl)-, Methyl ester

Chemical Property:

• PSA: 55.84000
• LogP: 1.69520

Purity/Quality:

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

Methyl1-Benzyl-2-(3-methoxy-3-oxopropyl)azetidine-2-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Azetidinepropanoic acid, 2-(Methoxycarbonyl)-1-(phenylMethyl)-, Methyl ester

There total 3 articles about 2-Azetidinepropanoic acid, 2-(Methoxycarbonyl)-1-(phenylMethyl)-, 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: 27.0%

Methyl 3-bromopropionate (3395-91-3) + methyl 2,4-dibromobutanoate (29547-04-4,70288-65-2) + benzylamine (100-46-9) → methyl N-benzyl-2-(2-methoxycarbonylethyl)azetidine-2-carboxylate (1353160-88-9,1376573-71-5)

Guidance literature:

methyl 2,4-dibromobutanoate; benzylamine; With triethylamine; In acetonitrile; for 4h; Heating;

Methyl 3-bromopropionate; With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diisopropyl amide; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1002/ejoc.201101278

Reference yield:

benzylamine (100-46-9) → methyl N-benzyl-2-(2-methoxycarbonylethyl)azetidine-2-carboxylate (1353160-88-9,1376573-71-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine / acetonitrile / 4 h / Reflux

2.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 1 h / -78 - -65 °C / Inert atmosphere

2.2: 16 h / -78 - 20 °C / Inert atmosphere

With triethylamine; lithium diisopropyl amide; In tetrahydrofuran; hexane; acetonitrile;

DOI:10.1016/j.tet.2012.03.111

Reference yield:

methyl 2,4-dibromobutanoate (29547-04-4,70288-65-2) → methyl N-benzyl-2-(2-methoxycarbonylethyl)azetidine-2-carboxylate (1353160-88-9,1376573-71-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine / acetonitrile / 4 h / Reflux

2.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 1 h / -78 - -65 °C / Inert atmosphere

2.2: 16 h / -78 - 20 °C / Inert atmosphere

With triethylamine; lithium diisopropyl amide; In tetrahydrofuran; hexane; acetonitrile;

DOI:10.1016/j.tet.2012.03.111

upstream raw materials:

Methyl 3-bromopropionate

methyl 2,4-dibromobutanoate

benzylamine

Refernces

• 1、 Nocquet, Pierre-Antoine,Hazelard, Damien,Compain, Philippe. "Synthesis of spirocyclopropyl γ-lactams by a highly stereoselective tandem intramolecular azetidine ring-opening/closing cascade reaction". scheme or table. p. 6619 - 6623. Retrieved 2011/12/16.