N-(tert-butyloxycarbonyl)-3-(3-hydroxy-4-benzyloxyphenyl)-L-alanine benzyl ester

Base Information

• Chemical Name: N-(tert-butyloxycarbonyl)-3-(3-hydroxy-4-benzyloxyphenyl)-L-alanine benzyl ester
• CAS No.: 224824-21-9
• Molecular Formula: C₂₈H₃₁NO₆
• Molecular Weight: 477.557
• Mol file: 224824-21-9.mol

Synonyms:N-(tert-butyloxycarbonyl)-3-(3-hydroxy-4-benzyloxyphenyl)-L-alanine benzyl ester

Chemical Property of N-(tert-butyloxycarbonyl)-3-(3-hydroxy-4-benzyloxyphenyl)-L-alanine benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(tert-butyloxycarbonyl)-3-(3-hydroxy-4-benzyloxyphenyl)-L-alanine benzyl ester

There total 10 articles about N-(tert-butyloxycarbonyl)-3-(3-hydroxy-4-benzyloxyphenyl)-L-alanine benzyl 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: 76.0%

benzyl bromide (100-39-0) + (S)-3-(4-benzyloxy-3-hydroxy-phenyl)-2-tert-butoxycarbonylamino-propionic acid (186689-02-1) → N-(tert-butyloxycarbonyl)-3-(3-hydroxy-4-benzyloxyphenyl)-L-alanine benzyl ester (224824-21-9)

Guidance literature:

With sodium hydrogencarbonate; In methylbutane;

DOI:10.1021/jo9902751

Reference yield: 74.0%

N-(tert-butyloxycarbonyl)-3-(3-acetoxy-4-benzyloxyphenyl)-L-alanine benzyl ester (269745-74-6) → N-(tert-butyloxycarbonyl)-3-(3-hydroxy-4-benzyloxyphenyl)-L-alanine benzyl ester (224824-21-9)

Guidance literature:

With ammonia; In methanol; for 1h;

DOI:10.1021/jo9913661

Reference yield:

(S)-3-(3-acetyl-4-hydroxyphenyl)-2-aminopropanoic acid hydrochloride (32404-28-7) → N-(tert-butyloxycarbonyl)-3-(3-hydroxy-4-benzyloxyphenyl)-L-alanine benzyl ester (224824-21-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 94 percent / NaHCO₃ / dioxane; H₂O / 20 °C

2: 91 percent / potassium carbonate; tetraethylammonium iodide / dimethylformamide / 20 °C

3: 81 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 168 h / 20 °C

4: 74 percent / NH₃ / methanol / 1 h

With tetraethylammonium iodide; ammonia; sodium hydrogencarbonate; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; In 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; 1: Substitution / 2: Esterification / 3: Oxidation / 4: Deacetylation;

DOI:10.1021/jo9913661

upstream raw materials:

benzyl bromide

(S)-3-(4-benzyloxy-3-hydroxy-phenyl)-2-tert-butoxycarbonylamino-propionic acid

N-(tert-butyloxycarbonyl)-3-(3-acetoxy-4-benzyloxyphenyl)-L-alanine benzyl ester

di-tert-butyl dicarbonate

Downstream raw materials:

Isodityrosine

(S,S)-isodityrosine bis hydrochloride

K-13

(S)-3-[4-benzyloxy-3-(4-{(S)-2-[(S)-1-tert-butoxycarbonyl-2-(4-hydroxy-phenyl)ethylcarbamoyl]-2-dibenzylaminoethyl}phenoxy)phenyl]-2-(tritylamino)-propionic acid benzyl ester