(2S)-2-{[(Benzyloxy)carbonyl](methyl)amino}-3-[4-(tert-butoxy)phenyl]propanoic acid

Base Information

• Chemical Name: (2S)-2-{[(Benzyloxy)carbonyl](methyl)amino}-3-[4-(tert-butoxy)phenyl]propanoic acid
• CAS No.: 67586-06-5
• Molecular Formula: C₂₂H₂₇NO₅
• Molecular Weight: 0
• Mol file: 67586-06-5.mol

Synonyms:(2S)-2-{[(Benzyloxy)carbonyl](methyl)amino}-3-[4-(tert-butoxy)phenyl]propanoic acid

Chemical Property of (2S)-2-{[(Benzyloxy)carbonyl](methyl)amino}-3-[4-(tert-butoxy)phenyl]propanoic acid

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2S)-2-{[(Benzyloxy)carbonyl](methyl)amino}-3-[4-(tert-butoxy)phenyl]propanoic acid

There total 2 articles about (2S)-2-{[(Benzyloxy)carbonyl](methyl)amino}-3-[4-(tert-butoxy)phenyl]propanoic acid 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: 78.0%

2-benzyloxycarbonylamino-3-(4-tert-butoxy-phenyl)-propionic acid methyl ester (5068-29-1) + methyl iodide (74-88-4) → N-Cbz-N-methyl-(O-tert-butyl)tyrosine (67586-06-5)

Guidance literature:

With sodium hydride; In tetrahydrofuran; for 16h; Ambient temperature;

DOI:10.1021/jm00110a005

Reference yield:

N-α-benzyloxycarbamoyl-O-t-butyl-L-tyrosine dicyclohexylammonium salt (16879-90-6,198828-72-7) + methyl iodide (74-88-4) → N-Cbz-N-methyl-(O-tert-butyl)tyrosine (67586-06-5)

Guidance literature:

With sodium hydride; citric acid; Yield given. Multistep reaction; 1.) AcOEt, 2.) THF, 24 h;

DOI:10.1248/cpb.29.3639

Reference yield:

N-Cbz-N-methyl-(O-tert-butyl)tyrosine (67586-06-5) → (S)-3-(4-tert-Butoxy-phenyl)-2-methylamino-propionic acid (343631-38-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In dichloromethane; for 13h;

DOI:10.1021/jm00110a005

upstream raw materials:

2-benzyloxycarbonylamino-3-(4-tert-butoxy-phenyl)-propionic acid methyl ester

methyl iodide

N-α-benzyloxycarbamoyl-O-t-butyl-L-tyrosine dicyclohexylammonium salt

Downstream raw materials:

[(S)-1-{(R)-1-[({[(S)-1-Benzyl-2-oxo-2-(N'-propionyl-hydrazino)-ethyl]-methyl-carbamoyl}-methyl)-carbamoyl]-ethylcarbamoyl}-2-(4-tert-butoxy-phenyl)-ethyl]-methyl-carbamic acid benzyl ester

(S)-3-(4-tert-Butoxy-phenyl)-2-methylamino-propionic acid

(S)-N-{(R)-1-[({[(S)-1-Benzyl-2-oxo-2-(N'-propionyl-hydrazino)-ethyl]-methyl-carbamoyl}-methyl)-carbamoyl]-ethyl}-3-(4-hydroxy-phenyl)-2-methylamino-propionamide

Refernces

• 1、 Shinagawa,Fujino,Ishii,Kawai. "Synthetic studies on enkephalin analogs. II. Enhanced analgesic activity of H-Tyr-D-Ala-Gly-Phe-NHNH-CO-CH2CH3 following n-methylation of Tyr and Phe". . p. 3639 - 3645. Retrieved 2007/10/02.