(S)-3-(3-bromo-5-(tert-butyl)phenyl)-3-(2-(3-guanidinobenzamido)acetamido)propanoic acid

Base Information

• Chemical Name: (S)-3-(3-bromo-5-(tert-butyl)phenyl)-3-(2-(3-guanidinobenzamido)acetamido)propanoic acid
• CAS No.: 1541196-91-1
• Molecular Formula: C₂₃H₂₈BrN₅O₄
• Molecular Weight: 518.41
• Mol file: 1541196-91-1.mol

Synonyms:(S)-3-(3-bromo-5-(tert-butyl)phenyl)-3-(2-(3-guanidinobenzamido)acetamido)propanoic acid

Chemical Property of (S)-3-(3-bromo-5-(tert-butyl)phenyl)-3-(2-(3-guanidinobenzamido)acetamido)propanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-(3-bromo-5-(tert-butyl)phenyl)-3-(2-(3-guanidinobenzamido)acetamido)propanoic acid

There total 19 articles about (S)-3-(3-bromo-5-(tert-butyl)phenyl)-3-(2-(3-guanidinobenzamido)acetamido)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: 52.0%

(S)-3-(3-bromo-5-tert-butylphenyl)-3-(2-tert-butoxycarbonylaminoacetylamino)propionic acid ethyl ester (1541197-73-2) + 3-Guanidinobenzoic acid (82957-07-1) → (S)-3-(3-bromo-5-(tert-butyl)phenyl)-3-(2-(3-guanidinobenzamido)acetamido)propanoic acid (1541196-91-1)

Guidance literature:

(S)-3-(3-bromo-5-tert-butylphenyl)-3-(2-tert-butoxycarbonylaminoacetylamino)propionic acid ethyl ester; With hydrogenchloride; In 1,4-dioxane; for 5h; Inert atmosphere;

3-Guanidinobenzoic acid; With benzotriazol-1-ol; diisopropyl-carbodiimide; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; for 64h; Inert atmosphere;

With lithium hydroxide; In tetrahydrofuran; Inert atmosphere;

DOI:10.1039/d0ob01495h

Reference yield:

(S)-ethyl 3-(3-bromo-5-(tert-butyl)phenyl)-3-(2-(3-guanidinobenzamido)acetamido)propanoate (1541198-84-8) → (S)-3-(3-bromo-5-(tert-butyl)phenyl)-3-(2-(3-guanidinobenzamido)acetamido)propanoic acid (1541196-91-1)

Guidance literature:

With lithium hydroxide monohydrate; In water; acetonitrile; at 20 ℃;

Reference yield:

3-(tert-butyl)benzaldehyde (23039-28-3) → (S)-3-(3-bromo-5-(tert-butyl)phenyl)-3-(2-(3-guanidinobenzamido)acetamido)propanoic acid (1541196-91-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: titanium(IV) isopropylate / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere

2.1: tetrahydrofuran / 18 h / 0 °C / Inert atmosphere; Reflux

3.1: hydrogenchloride / diethyl ether; 1,4-dioxane / 0.33 h / Inert atmosphere

3.2: 17 h / 20 °C / Inert atmosphere; Cooling with ice

4.1: copper(ll) bromide / water; methanol / 16 h / 70 °C / Inert atmosphere

4.2: 16 h / Inert atmosphere

5.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / acetonitrile / 0.25 h / Inert atmosphere; Cooling with ice

5.2: 16 h / 20 °C / Inert atmosphere

6.1: hydrogenchloride / 1,4-dioxane / 5 h / Inert atmosphere

6.2: 64 h / 20 °C / Inert atmosphere

6.3: Inert atmosphere

With titanium(IV) isopropylate; hydrogenchloride; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; copper(ll) bromide; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; water; acetonitrile; 2.1: |Reformatsky Reaction;

DOI:10.1039/d0ob01495h

upstream raw materials:

3-(3-benzoylthioureido)benzoic acid

1-(3-carboxyphenyl)-2-thiourea

3-(imino(methylthio)methylamino)benzoic acid

(S)-3-(2-aminoacetylamino)-3-(3-bromo-5-tert-butylphenyl)propionic acid ethyl ester hydrochloride salt