(S)-methyl 3-(4-(2-bromoethoxy)phenyl)-2-((tert-butoxycarbonyl)amino)propanoate

Base Information

• Chemical Name: (S)-methyl 3-(4-(2-bromoethoxy)phenyl)-2-((tert-butoxycarbonyl)amino)propanoate
• CAS No.: 1269631-36-8
• Molecular Formula: C₁₇H₂₄BrNO₅
• Molecular Weight: 402.285
• Mol file: 1269631-36-8.mol

Synonyms:(S)-methyl 3-(4-(2-bromoethoxy)phenyl)-2-((tert-butoxycarbonyl)amino)propanoate

Chemical Property of (S)-methyl 3-(4-(2-bromoethoxy)phenyl)-2-((tert-butoxycarbonyl)amino)propanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-methyl 3-(4-(2-bromoethoxy)phenyl)-2-((tert-butoxycarbonyl)amino)propanoate

There total 3 articles about (S)-methyl 3-(4-(2-bromoethoxy)phenyl)-2-((tert-butoxycarbonyl)amino)propanoate 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: 89.0%

(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester (4326-36-7) + ethylene dibromide (106-93-4) → (S)-methyl 3-(4-(2-bromoethoxy)phenyl)-2-((tert-butoxycarbonyl)amino)propanoate (1269631-36-8)

Guidance literature:

With 18-crown-6 ether; potassium carbonate; In N,N-dimethyl-formamide; at 80 ℃; for 22h;

DOI:10.1021/acs.jmedchem.6b00968

Reference yield: 50.0%

(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester (4326-36-7) + 2-bromoethanol (540-51-2) → (S)-methyl 3-(4-(2-bromoethoxy)phenyl)-2-((tert-butoxycarbonyl)amino)propanoate (1269631-36-8)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; toluene; at 0 - 25 ℃;

Reference yield:

Boc-Tyr-OH (3978-80-1) → (S)-methyl 3-(4-(2-bromoethoxy)phenyl)-2-((tert-butoxycarbonyl)amino)propanoate (1269631-36-8)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate / N,N-dimethyl-formamide / 0.57 h / 20 °C / Inert atmosphere

2: 18-crown-6 ether; potassium carbonate / N,N-dimethyl-formamide / 22 h / 80 °C

With 18-crown-6 ether; potassium carbonate; In N,N-dimethyl-formamide; 2: |Williamson Ether Synthesis;

DOI:10.1021/acs.jmedchem.6b00968

upstream raw materials:

(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

ethylene dibromide

2-bromoethanol

Boc-Tyr-OH

Downstream raw materials:

4-(2-bromoethoxy)phenylalanine

C₁₇H₂₄INO₅

O-(2-iodoethyl)-L-tyrosine

C₅₁H₇₇N₁₅O₁₁S