(S)-2-(tert-butyloxycarbonylamino)-3-(5-iodo-2-methoxyphenyl)-propionic acid

Base Information

• Chemical Name: (S)-2-(tert-butyloxycarbonylamino)-3-(5-iodo-2-methoxyphenyl)-propionic acid
• CAS No.: 1095089-24-9
• Molecular Formula: C₁₅H₂₀INO₅
• Molecular Weight: 421.232
• Mol file: 1095089-24-9.mol

Synonyms:(S)-2-(tert-butyloxycarbonylamino)-3-(5-iodo-2-methoxyphenyl)-propionic acid

Chemical Property of (S)-2-(tert-butyloxycarbonylamino)-3-(5-iodo-2-methoxyphenyl)-propionic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-(tert-butyloxycarbonylamino)-3-(5-iodo-2-methoxyphenyl)-propionic acid

There total 1 articles about (S)-2-(tert-butyloxycarbonylamino)-3-(5-iodo-2-methoxyphenyl)-propionic 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: 92.0%

di-tert-butyl dicarbonate (24424-99-5) + (S)-2-amino-3-(5'-iodo-2'-methoxyphenyl)propanoic acid hydrochloride (1095089-33-0) → (S)-2-(tert-butyloxycarbonylamino)-3-(5-iodo-2-methoxyphenyl)-propionic acid (1095089-24-9)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; water; for 16h; Inert atmosphere;

DOI:10.1039/b811583d

Reference yield: 97.0%

(S)-2-(tert-butyloxycarbonylamino)-3-(5-iodo-2-methoxyphenyl)-propionic acid (1095089-24-9) + methyl iodide (74-88-4) → (S)-2-(tert-butyloxycarbonyl)amino-3-(2-methoxy-5-iodphenyl)propionic acid methyl ester (1095089-26-1)

Guidance literature:

With potassium carbonate; In acetone; at 56 ℃; for 16h; Inert atmosphere;

DOI:10.1039/b811583d

Reference yield:

(S)-2-(tert-butyloxycarbonylamino)-3-(5-iodo-2-methoxyphenyl)-propionic acid (1095089-24-9) → (4S,7S,10S)-10-benzyloxycarbonylamino-11,21-bis-methoxy-7-methyl-5,8-diaza-6,9-dioxo-1,2(4,2)-dibenzenacycloundecaphane-4-methyl carboxylate

Guidance literature:

Multi-step reaction with 6 steps

1: potassium carbonate / acetone / 20 h / Inert atmosphere; Reflux

2: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / dimethyl sulfoxide / 4 h / 80 °C / Inert atmosphere

3: caesium carbonate; palladium diacetate; tris-(o-tolyl)phosphine / 1,4-dioxane; water / 8 h / 80 °C / Inert atmosphere

4: benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere

5: hydrogenchloride / 1,4-dioxane; water / 4 h / 20 °C / Inert atmosphere

6: N-ethyl-N,N-diisopropylamine; HATU; 1-hydroxy-7-aza-benzotriazole / dichloromethane / 28 h / 20 °C / Inert atmosphere

With hydrogenchloride; 1-hydroxy-7-aza-benzotriazole; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; palladium diacetate; potassium carbonate; benzotriazol-1-ol; caesium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; HATU; tris-(o-tolyl)phosphine; In 1,4-dioxane; dichloromethane; water; dimethyl sulfoxide; acetone; 3: |Suzuki Coupling;

DOI:10.1002/asia.201000908

upstream raw materials:

di-tert-butyl dicarbonate

(S)-2-amino-3-(5'-iodo-2'-methoxyphenyl)propanoic acid hydrochloride

Downstream raw materials:

(S)-2-(tert-butyloxycarbonyl)amino-3-(2-methoxy-5-iodphenyl)propionic acid methyl ester

(2S,2’’’S)-2-(benzyloxcarbonylamino)-3-(4’,4’’-bis-methoxy-3’’-[tert-butyloxycarbonylamino-2’’’-methoxycarbonylethyl]-biphenyl-3’-yl)-propionic acid

C₄₉H₇₀N₆O₁₂Si

(4S,7S,10S,2’R)-10-benzyoxycarbonylamino-1¹,2¹-bis-methoxy-7-[3’-azido-2’-(tert-butyldimethyl-silyloxy)propyl]-5,8-diaza-6,9-dioxo-1,2(4,2)-dibenzenacycloundecaphane-4-methyl carboxylate