(S)-2-tert-Butoxycarbonylamino-succinic acid bis-[2-(4-acetyl-2-nitro-phenyl)-ethyl] ester

Base Information

• Chemical Name: (S)-2-tert-Butoxycarbonylamino-succinic acid bis-[2-(4-acetyl-2-nitro-phenyl)-ethyl] ester
• CAS No.: 156589-18-3
• Molecular Formula: C₂₉H₃₃N₃O₁₂
• Molecular Weight: 615.594
• Mol file: 156589-18-3.mol

Synonyms:(S)-2-tert-Butoxycarbonylamino-succinic acid bis-[2-(4-acetyl-2-nitro-phenyl)-ethyl] ester

Chemical Property of (S)-2-tert-Butoxycarbonylamino-succinic acid bis-[2-(4-acetyl-2-nitro-phenyl)-ethyl] ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-tert-Butoxycarbonylamino-succinic acid bis-[2-(4-acetyl-2-nitro-phenyl)-ethyl] ester

There total 4 articles about (S)-2-tert-Butoxycarbonylamino-succinic acid bis-[2-(4-acetyl-2-nitro-phenyl)-ethyl] 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: 68.0%

Boc-Asp-OH (13726-67-5) + 1-<4-(2-hydroxyethyl)-3-nitrophenyl>-1-ethanone (156589-17-2) → (S)-2-tert-Butoxycarbonylamino-succinic acid bis-[2-(4-acetyl-2-nitro-phenyl)-ethyl] ester (156589-18-3)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; 2 h, 0 deg C and room t. overnight;

DOI:10.1055/s-1993-26039

Reference yield:

2-phenylethanol (60-12-8) → (S)-2-tert-Butoxycarbonylamino-succinic acid bis-[2-(4-acetyl-2-nitro-phenyl)-ethyl] ester (156589-18-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 60 percent / AlCl₃ / CH₂Cl₂ / in ice bath, 30 min and 1 h, room t.

2: 60 percent / fuming HNO₃, 96percent H₂SO₄ / acetic anhydride / 1 h / -20 °C

3: 77 percent / conc. aq. HCl/MeOH / 2 h / 50 - 60 °C

4: 68 percent / DCC/DMAP / CH₂Cl₂ / 2 h, 0 deg C and room t. overnight

With hydrogenchloride; methanol; dmap; aluminium trichloride; sulfuric acid; nitric acid; dicyclohexyl-carbodiimide; In dichloromethane; acetic anhydride;

DOI:10.1055/s-1993-26039

Reference yield:

β-(4-acetylphenyl)ethyl acetate (73823-79-7) → (S)-2-tert-Butoxycarbonylamino-succinic acid bis-[2-(4-acetyl-2-nitro-phenyl)-ethyl] ester (156589-18-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 60 percent / fuming HNO₃, 96percent H₂SO₄ / acetic anhydride / 1 h / -20 °C

2: 77 percent / conc. aq. HCl/MeOH / 2 h / 50 - 60 °C

3: 68 percent / DCC/DMAP / CH₂Cl₂ / 2 h, 0 deg C and room t. overnight

With hydrogenchloride; methanol; dmap; sulfuric acid; nitric acid; dicyclohexyl-carbodiimide; In dichloromethane; acetic anhydride;

DOI:10.1055/s-1993-26039

upstream raw materials:

Boc-Asp-OH

1-<4-(2-hydroxyethyl)-3-nitrophenyl>-1-ethanone

2-phenylethanol

β-(4-acetylphenyl)ethyl acetate

Downstream raw materials:

(S)-2-tert-Butoxycarbonylamino-succinic acid 4-[2-(4-acetyl-2-nitro-phenyl)-ethyl] ester

Refernces