Benzenepropanoic acid, a-azido-, methyl ester, (R)-

Base Information

• Chemical Name: Benzenepropanoic acid, a-azido-, methyl ester, (R)-
• CAS No.: 124790-74-5
• Molecular Formula: C10H11N3O2
• Molecular Weight: 205.216
• Mol file: 124790-74-5.mol

Synonyms:

Chemical Property of Benzenepropanoic acid, a-azido-, methyl ester, (R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Benzenepropanoic acid, a-azido-, methyl ester, (R)-

There total 15 articles about Benzenepropanoic acid, a-azido-, methyl ester, (R)- 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: 92.0%

(S)-2-bromo-3-penylpropanoic acid methyl ester (124916-61-6) → (R)-2-azido-3-phenylpropionic acid methyl ester (124790-74-5)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 40 ℃; for 1h;

DOI:10.1039/c9gc00755e

Reference yield: 85.0%

D-phenylalanine methyl ester hydrochloride (13033-84-6) → (R)-2-azido-3-phenylpropionic acid methyl ester (124790-74-5)

Guidance literature:

With triflic azide; copper(II) sulfate; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; for 15h;

DOI:10.1016/j.tet.2006.07.007

Reference yield:

2,2-dichloro-3-phenylpropionaldehyde (76043-69-1) → (R)-2-azido-3-phenylpropionic acid methyl ester (124790-74-5)

Guidance literature:

Multi-step reaction with 3 steps

1: chiral azolium salt; 2,6-dibromo-4-methylphenol; KH / 18-crown-6 / toluene / 19 h / 23 °C

2: NaN₃ / dimethylformamide

With sodium azide; chiral azolium salt; 3,5-dibromo-4-hydroxytoluene; potassium hydride; 18-crown-6 ether; In N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja055918a

upstream raw materials:

(S)-methyl 2-((p-nitrobenzene)sulfonyl)oxy 3-phenylpropanoate

(R)-2-bromo-3-phenylpropionic acid methyl ester

(S)-2-methanesulfonyloxy-3-phenylpropionic acid methyl ester

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

Downstream raw materials:

D-phenylalanine methyl ester

(R)-2-azido-3-phenylpropionic acid

(R)-phenylalanine isopropyl ester

(S)-2-Azido-3-phenyl-propionic acid (S)-2-((R)-2-azido-3-phenyl-propionylamino)-3-(4-methoxy-phenyl)-propyl ester

Refernces

• 1、 Park, Yun Ji,Yang, Jung Woon. "Glycerol conversion to high-value chemicals: The implication of unnatural α-amino acid syntheses using natural resources". . p. 2615 - 2620. Retrieved 2019/06/03.
• 2、 Gurjar, Mukund K,Karmakar, Sukhen,Mohapatra, Debendra K,Phalgune, Usha D. "A novel application of a [3+2] cycloaddition reaction for the synthesis of the piperazinone rings of pseudotheonamides A1 and A2". . p. 1897 - 1900. Retrieved 2007/10/03.