N-Acetyl-DL-serine methyl ester

Base Information

• Chemical Name: N-Acetyl-DL-serine methyl ester
• CAS No.: 55299-56-4
• Molecular Formula: C₆H₁₁NO₄
• Molecular Weight: 161.158
• Mol file: 55299-56-4.mol

Synonyms:N-(acetyl)-L-serine methyl ester;N-acetyl-L-serine methyl ester;L-N-acetylserine methyl ester;

Chemical Property of N-Acetyl-DL-serine methyl ester

Chemical Property:

• Boiling Point: 376.3±27.0 °C(Predicted)
• PKA: 13.83±0.10(Predicted)
• PSA: 75.63000
• Density: 1.194±0.06 g/cm3(Predicted)
• LogP: -0.95270

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-Acetyl-DL-serine methyl ester

There total 13 articles about N-Acetyl-DL-serine 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: 93.0%

methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride (5680-80-8) + acetic acid (64-19-7,77671-22-8) → (S)-methyl 2-acetamido-3-hydroxypropanoate (2311-26-4,54322-41-7,55299-56-4,288402-26-6)

Guidance literature:

With triethylamine; dicyclohexyl-carbodiimide; In dichloromethane;

DOI:10.1021/jo00049a019

Reference yield: 84.0%

methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride (5680-80-8) + acetyl chloride (75-36-5) → (S)-methyl 2-acetamido-3-hydroxypropanoate (2311-26-4,54322-41-7,55299-56-4,288402-26-6)

Guidance literature:

With triethylamine; In dichloromethane; at -5 - 20 ℃; for 2h;

DOI:10.1016/j.tet.2008.07.015

Reference yield: 83.0%

(S)-serine methyl ester (2788-84-3) + benzylidene 1,1-diacetate (581-55-5) → (S)-methyl 2-acetamido-3-hydroxypropanoate (2311-26-4,54322-41-7,55299-56-4,288402-26-6)

Guidance literature:

In neat (no solvent); at 70 ℃; for 16h;

DOI:10.1016/j.tet.2018.05.044

upstream raw materials:

N-Acetyl-3-O-p-tolylsulfonyl-DL-serin-methylester

diazomethane

2-aminomalonic acid

acetic anhydride

Downstream raw materials:

(S)-methyl 2-acetamido-3-(formyloxy)propanoate

N-acetyl-L-serine

2-acetamido-N-benzyl-3-methoxypropionamide

(+)-2-acetamido-3-azidopropanoic acid methyl ester

Refernces

• 1、 Sayama, Misa,Uwamizu, Akiharu,Ikubo, Masaya,Chen, Luying,Yan, Ge,Otani, Yuko,Inoue, Asuka,Aoki, Junken,Ohwada, Tomohiko. "Switching Lysophosphatidylserine G Protein-Coupled Receptor Agonists to Antagonists by Acylation of the Hydrophilic Serine Amine". . p. 10059 - 10101. Retrieved 2021/07/28.
• 2、 Nathanael, Joses G.,Wille, Uta. "Oxidative Damage in Aliphatic Amino Acids and Di- and Tripeptides by the Environmental Free Radical Oxidant NO3?: the Role of the Amide Bond Revealed by Kinetic and Computational Studies". . p. 3405 - 3418. Retrieved 2019/03/11.