N-Chloroacetyl-L-phenylalanine

Base Information

• Chemical Name: N-Chloroacetyl-L-phenylalanine
• CAS No.: 721-65-3
• Molecular Formula: C11H12ClNO3
• Molecular Weight: 241.674
• Hs Code.: 2924299090
• Nikkaji Number: J231.868G
• Mol file: 721-65-3.mol

Synonyms:N-Chloroacetyl-L-phenylalanine;721-65-3;(2S)-2-[(2-chloroacetyl)amino]-3-phenylpropanoic acid;N-(Chloroacetyl)phenylalanine;Chloracetylphenylalanin;SCHEMBL995228;(2-Chloroacetyl)-L-phenylalanine;Alanine, N-(chloroacetyl)-3-phenyl-, DL-;CS-0362848

Chemical Property of N-Chloroacetyl-L-phenylalanine

Chemical Property:

• PSA: 66.40000
• LogP: 1.42820
• Storage Temp.: −20°C
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 241.0505709
• Heavy Atom Count: 16
• Complexity: 252

Purity/Quality:

98.5% ^*data from raw suppliers

N-CHLOROACETYL-L-PHENYLALANINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CC(C(=O)O)NC(=O)CCl
• Isomeric SMILES: C1=CC=C(C=C1)C[C@@H](C(=O)O)NC(=O)CCl

Technology Process of N-Chloroacetyl-L-phenylalanine

There total 2 articles about N-Chloroacetyl-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: 61.0%

L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) + chloroacetyl chloride (79-04-9) → (S)-2-(2-chloroacetamido)-4-methylpentanoic acid (721-65-3)

Guidance literature:

In tetrahydrofuran; for 2h; Reflux;

DOI:10.1055/s-0031-1290446

Reference yield:

→ (S)-2-(2-chloroacetamido)-4-methylpentanoic acid (721-65-3)

Guidance literature:

aus L-Phenylalanin, Chloressigsaeurechlorid;

DOI:10.1016/S0040-4039(01)86139-6

Reference yield: 97.0%

(S)-2-(2-chloroacetamido)-4-methylpentanoic acid (721-65-3) + phosphorous acid trimethyl ester (121-45-9) → (S)-2-[2-(Dimethoxy-phosphoryl)-acetylamino]-3-phenyl-propionic acid methyl ester (82283-65-6)

Guidance literature:

for 3h; Heating;

DOI:10.1055/s-1982-29754

upstream raw materials:

L-phenylalanine

chloroacetyl chloride

Downstream raw materials:

N-(2-benzooxazol-2-ylsulfanyl-acetyl)-L-phenylalanine

4S-3-chloroacetyl-4-benzyl-5-oxazolidinone

MCA-Phe-Met-OMe

(S)-2-[2-(Dimethoxy-phosphoryl)-acetylamino]-3-phenyl-propionic acid methyl ester

Refernces

• 1、 Beagle, Lucas K.,Hansen, Finn K.,Monbaliu, Jean-Christophe M.,Desrosiers, Michael P.,Phillips, Angela M.,Stevens, Christian V.,Katritzky, Alan R.. "Efficient synthesis of 2,5-diketopiperazines by Staudinger-mediated cyclization". supporting information. p. 2337 - 2340. Retrieved 2013/07/11.