L-Phenylalanine, N-acetyl-, cyanomethyl ester

Base Information

• Chemical Name: L-Phenylalanine, N-acetyl-, cyanomethyl ester
• CAS No.: 61781-58-6
• Molecular Formula: C13H14N2O3
• Molecular Weight: 246.266
• Mol file: 61781-58-6.mol

Synonyms:

Chemical Property of L-Phenylalanine, N-acetyl-, cyanomethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of L-Phenylalanine, N-acetyl-, cyanomethyl ester

There total 2 articles about L-Phenylalanine, N-acetyl-, cyanomethyl 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%

(S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3) + chloroacetonitrile (107-14-2) → (S)-cyanomethyl 2-acetamido-3-phenylpropanoate (61781-58-6)

Guidance literature:

With triethylamine; In acetonitrile; at 0 - 20 ℃; for 4.5h;

DOI:10.1055/s-0036-1589123

Reference yield:

(S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3) + cyanomethyl bromide (590-17-0) → (S)-cyanomethyl 2-acetamido-3-phenylpropanoate (61781-58-6)

Guidance literature:

With caesium carbonate; at 20 ℃;

DOI:10.1002/ejoc.201601148

Reference yield: 89.0%

(S)-cyanomethyl 2-acetamido-3-phenylpropanoate (61781-58-6) → 2-amino-2-thioxoethyl N-acetyl-L-phenylalaninate (1130858-12-6)

Guidance literature:

(S)-cyanomethyl 2-acetamido-3-phenylpropanoate; With Lawessons reagent; boron trifluoride diethyl etherate; In tetrahydrofuran; 1,2-dimethoxyethane; at 40 ℃; for 4h; Inert atmosphere;

With sodium hydrogencarbonate; In tetrahydrofuran; 1,2-dimethoxyethane; at 20 ℃; for 0.333333h; Inert atmosphere;

DOI:10.1055/s-0028-1083253

upstream raw materials:

(S)-2-acetylamino-3-phenylpropanoic acid

chloroacetonitrile

cyanomethyl bromide

Downstream raw materials:

N-acetyl-L-phenylalanine carbamoylmethyl ester

2-amino-2-thioxoethyl N-acetyl-L-phenylalaninate

(S)-(2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-3-yl 2-acetamido-3-phenylpropanoate

Refernces

• 1、 -. "Methods of modifying N-termini of a peptide or protein using transferases". Page/Page column 20; 21. . Retrieved 2016/08/03.
• 2、 Wagner, Anne M.,Fegley, Mark W.,Warner, John B.,Grindley, Christina L. J.,Marotta, Nicholas P.,Petersson, E. James. "N-terminal protein modification using simple aminoacyl transferase substrates". supporting information; experimental part. p. 15139 - 15147. Retrieved 2011/11/06.