L-Serine, N-benzoyl-, phenylmethyl ester

Base Information

• Chemical Name: L-Serine, N-benzoyl-, phenylmethyl ester
• CAS No.: 138739-05-6
• Molecular Formula: C17H17NO4
• Molecular Weight: 299.326
• Mol file: 138739-05-6.mol

Synonyms:

Chemical Property of L-Serine, N-benzoyl-, phenylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of L-Serine, N-benzoyl-, phenylmethyl ester

There total 3 articles about L-Serine, N-benzoyl-, phenylmethyl 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: 97.0%

L-serine benzyl ester hydrochloride (60022-62-0,879278-55-4,151651-44-4) + benzoyl chloride (98-88-4) → 2-benzoylamino-3-hydroxypropionic acid benzyl ester (138739-05-6)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; for 3.5h;

DOI:10.1039/a904730a

Reference yield: 48.0%

(S)-2-benzoylamino-3-hydroxypropionic acid (4877-23-0) + benzyl bromide (100-39-0) → 2-benzoylamino-3-hydroxypropionic acid benzyl ester (138739-05-6)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; triethylamine; In tetrahydrofuran; at 20 ℃; for 17.1h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.1c00347

Reference yield:

benzyl chloride (100-44-7) → 2-benzoylamino-3-hydroxypropionic acid benzyl ester (138739-05-6)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate / water / 18 h / 20 °C

2: triethylamine; tetra-(n-butyl)ammonium iodide / tetrahydrofuran / 17.1 h / 20 °C / Inert atmosphere

With tetra-(n-butyl)ammonium iodide; potassium carbonate; triethylamine; In tetrahydrofuran; water;

DOI:10.1021/acs.jmedchem.1c00347

upstream raw materials:

L-serine benzyl ester hydrochloride

benzoyl chloride

(S)-2-benzoylamino-3-hydroxypropionic acid

benzyl bromide

Downstream raw materials:

benzyl N-benzoyldehydroalanine

(S)-benzyl 2-phenyl-4,5-dihydrooxazole-4-carboxylate

2-phenyl-1,3-oxazole-4-carboxylic acid

benzyl 2-phenyloxazole-4-carboxylate

Refernces

• 1、 Moraski, Garrett C.,Markley, Lowell D.,Chang, Mayland,Cho, Sanghyun,Franzblau, Scott G.,Hwang, Chang Hwa,Boshoff, Helena,Miller, Marvin J.. "Generation and exploration of new classes of antitubercular agents: The optimization of oxazolines, oxazoles, thiazolines, thiazoles to imidazo[1,2-a]pyridines and isomeric 5,6-fused scaffolds". supporting information; experimental part. p. 2214 - 2220. Retrieved 2012/05/20.
• 2、 Stefely, Jonathan A.,Palchaudhuri, Rahul,Miller, Patricia A.,Peterson, Rebecca J.,Moraski, Garrett C.,Hergenrother, Paul J.,Miller, Marvin J.. "N -((1-benzyl-1 H -1,2,3-triazol-4-yl)methyl)arylamide as a new scaffold that provides rapid access to antimicrotubule agents: Synthesis and evaluation of antiproliferative activity against select cancer cell lines". supporting information; experimental part. p. 3389 - 3395. Retrieved 2010/09/04.