(S)-2-Amino-3-[4-(2-azido-ethoxy)-3-nitro-benzoylamino]-propionic acid benzyl ester

Base Information

• Chemical Name: (S)-2-Amino-3-[4-(2-azido-ethoxy)-3-nitro-benzoylamino]-propionic acid benzyl ester
• CAS No.: 215050-05-8
• Molecular Formula: C₁₉H₂₀N₆O₆
• Molecular Weight: 428.404
• Mol file: 215050-05-8.mol

Synonyms:(S)-2-Amino-3-[4-(2-azido-ethoxy)-3-nitro-benzoylamino]-propionic acid benzyl ester

Chemical Property of (S)-2-Amino-3-[4-(2-azido-ethoxy)-3-nitro-benzoylamino]-propionic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-Amino-3-[4-(2-azido-ethoxy)-3-nitro-benzoylamino]-propionic acid benzyl ester

There total 7 articles about (S)-2-Amino-3-[4-(2-azido-ethoxy)-3-nitro-benzoylamino]-propionic acid 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: 84.0%

3-[4-(2-azido-ethoxy)-3-nitro-benzoylamino]-2-tert-butoxycarbonylamino-propionic acid benzyl ester (215050-02-5) → (S)-2-Amino-3-[4-(2-azido-ethoxy)-3-nitro-benzoylamino]-propionic acid benzyl ester (215050-05-8)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 25 ℃; for 2h; Acid hydrolysis;

DOI:10.1016/S0968-0896(98)00090-X

Reference yield:

3-nitro-4-fluorobenzoic acid (453-71-4) → (S)-2-Amino-3-[4-(2-azido-ethoxy)-3-nitro-benzoylamino]-propionic acid benzyl ester (215050-05-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 98 percent / toluene / 8 h / 80 °C

2: 73 percent / molecular sieves 4A / Bu₄NF / dimethylformamide / 4 h / 25 °C

3: 99 percent / LiOH*H₂O / H₂O; dioxane / 4 h / 25 °C

4: 82 percent / DCC / 4-DMAP / CH₂Cl₂ / 4 h / 25 °C

5: 84 percent / CF₃CO₂H / CH₂Cl₂ / 2 h / 25 °C / Acid hydrolysis

With lithium hydroxide; 4 A molecular sieve; dicyclohexyl-carbodiimide; trifluoroacetic acid; dmap; tetrabutyl ammonium fluoride; In 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; toluene; 1: Esterification / 2: Substitution / 3: Hydrolysis / 4: Substitution / 5: Hydrolysis;

DOI:10.1016/S0968-0896(98)00090-X

Reference yield:

N-[(1,1-dimethylethoxycarbonyl)amino]-L-asparagine benzyl ester (13512-57-7) → (S)-2-Amino-3-[4-(2-azido-ethoxy)-3-nitro-benzoylamino]-propionic acid benzyl ester (215050-05-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 41 percent / PhI(OCOCF₃)2; pyridine / dimethylformamide; H₂O / 3.5 h / 25 °C

2: 82 percent / DCC / 4-DMAP / CH₂Cl₂ / 4 h / 25 °C

3: 84 percent / CF₃CO₂H / CH₂Cl₂ / 2 h / 25 °C / Acid hydrolysis

With pyridine; dicyclohexyl-carbodiimide; trifluoroacetic acid; bis-[(trifluoroacetoxy)iodo]benzene; dmap; In dichloromethane; water; N,N-dimethyl-formamide; 1: Reduction / 2: Substitution / 3: Hydrolysis;

DOI:10.1016/S0968-0896(98)00090-X

upstream raw materials:

3-[4-(2-azido-ethoxy)-3-nitro-benzoylamino]-2-tert-butoxycarbonylamino-propionic acid benzyl ester

N-[(1,1-dimethylethoxycarbonyl)amino]-L-asparagine benzyl ester

3-nitro-4-fluorobenzoic acid

4-fluoro-3-nitro-benzoic acid methyl ester

Downstream raw materials:

(S)-3-[4-(2-Azido-ethoxy)-3-nitro-benzoylamino]-2-(naphthalene-1-sulfonylamino)-propionic acid benzyl ester

(S)-3-[4-(2-Azido-ethoxy)-3-nitro-benzoylamino]-2-benzenesulfonylamino-propionic acid benzyl ester

(S)-3-[4-(2-Amino-ethoxy)-3-nitro-benzoylamino]-2-(naphthalene-1-sulfonylamino)-propionic acid benzyl ester

(S)-3-[4-(2-Amino-ethoxy)-3-nitro-benzoylamino]-2-benzenesulfonylamino-propionic acid benzyl ester