N²-(1-D-carboxyethyl)-L-phenylalanine

Base Information

• Chemical Name: N²-(1-D-carboxyethyl)-L-phenylalanine
• CAS No.: 103954-23-0
• Molecular Formula: C₁₂H₁₅NO₄*ClH
• Molecular Weight: 273.716
• Mol file: 103954-23-0.mol

Synonyms:N²-(1-D-carboxyethyl)-L-phenylalanine

Chemical Property of N²-(1-D-carboxyethyl)-L-phenylalanine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N²-(1-D-carboxyethyl)-L-phenylalanine

There total 7 articles about N²-(1-D-carboxyethyl)-L-phenylalanine 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: 90.0%

methyl ((R)-1-methoxy-1-oxopropan-2-yl)-L-phenylalaninate → N2-(1-D-carboxyethyl)-L-phenylalanine (103954-23-0)

Guidance literature:

methyl ((R)-1-methoxy-1-oxopropan-2-yl)-L-phenylalaninate; With lithium hydroxide; In methanol; water; for 20h; Inert atmosphere;

With hydrogenchloride; In water; pH=1; Inert atmosphere;

DOI:10.1002/ejoc.202100259

Reference yield:

methyl N-(tert-butyloxycarbonyl)-N-((R)-1-methoxy-1-oxopropan-2-yl)-L-phenylalaninate → N2-(1-D-carboxyethyl)-L-phenylalanine (103954-23-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.33 h / 0 °C / Schlenk technique; Inert atmosphere

2.1: lithium hydroxide / methanol; water / 20 h / Inert atmosphere

2.2: pH 1 / Inert atmosphere

With trimethylsilyl trifluoromethanesulfonate; lithium hydroxide; In methanol; dichloromethane; water;

DOI:10.1002/ejoc.202100259

Reference yield:

methyl ((E)-pent-3-en-2-yl)-L-phenylalaninate → N2-(1-D-carboxyethyl)-L-phenylalanine (103954-23-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 16 h / 80 °C / Inert atmosphere

2.1: sodium hydroxide; ozone / dichloromethane / 1 h / -78 °C / Inert atmosphere

3.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.33 h / 0 °C / Schlenk technique; Inert atmosphere

4.1: lithium hydroxide / methanol; water / 20 h / Inert atmosphere

4.2: pH 1 / Inert atmosphere

With trimethylsilyl trifluoromethanesulfonate; ozone; sodium hydroxide; lithium hydroxide; In methanol; dichloromethane; water;

DOI:10.1002/ejoc.202100259

upstream raw materials:

methyl (2S)-2-amino-3-phenylpropanoate

ethyl (S)-lactate triflate

methyl (2S)-2-amino-3-phenylpropanoate hydrochloride

Refernces

• 1、 Effenberger, Franz,Burkard, Ulrike. "Amino Acids, 5. - Stereoselective Synthesis of α,α'-Imino Dicarboxylic Acids". . p. 334 - 358. Retrieved 2007/10/02.