3-{3-[4-((S)-2-Acetylamino-2-methoxycarbonyl-ethyl)-phenoxy]-4-benzyloxycarbonylamino-phenyl}-2-tert-butoxycarbonylamino-propionic acid ethyl ester

Base Information

• Chemical Name: 3-{3-[4-((S)-2-Acetylamino-2-methoxycarbonyl-ethyl)-phenoxy]-4-benzyloxycarbonylamino-phenyl}-2-tert-butoxycarbonylamino-propionic acid ethyl ester
• CAS No.: 144333-47-1
• Molecular Formula: C₃₆H₄₃N₃O₁₀
• Molecular Weight: 677.752
• Mol file: 144333-47-1.mol

Synonyms:

Chemical Property of 3-{3-[4-((S)-2-Acetylamino-2-methoxycarbonyl-ethyl)-phenoxy]-4-benzyloxycarbonylamino-phenyl}-2-tert-butoxycarbonylamino-propionic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-{3-[4-((S)-2-Acetylamino-2-methoxycarbonyl-ethyl)-phenoxy]-4-benzyloxycarbonylamino-phenyl}-2-tert-butoxycarbonylamino-propionic acid ethyl ester

There total 5 articles about 3-{3-[4-((S)-2-Acetylamino-2-methoxycarbonyl-ethyl)-phenoxy]-4-benzyloxycarbonylamino-phenyl}-2-tert-butoxycarbonylamino-propionic acid 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: 86.0%

benzyl chloroformate (501-53-1,94274-21-2) + 3-{3-[4-((S)-2-Acetylamino-2-methoxycarbonyl-ethyl)-phenoxy]-4-amino-phenyl}-2-tert-butoxycarbonylamino-propionic acid ethyl ester (144333-37-9,144356-69-4) → 3-{3-[4-((S)-2-Acetylamino-2-methoxycarbonyl-ethyl)-phenoxy]-4-benzyloxycarbonylamino-phenyl}-2-tert-butoxycarbonylamino-propionic acid ethyl ester (144333-47-1,144333-48-2)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 0 ℃; for 3h;

DOI:10.1016/S0040-4039(00)61289-3

Reference yield:

3-bromo-4-nitrotoluene (40385-54-4) → 3-{3-[4-((S)-2-Acetylamino-2-methoxycarbonyl-ethyl)-phenoxy]-4-benzyloxycarbonylamino-phenyl}-2-tert-butoxycarbonylamino-propionic acid ethyl ester (144333-47-1,144333-48-2)

Guidance literature:

Multi-step reaction with 5 steps

1: CrO₃, conc. H₂SO₄, Ac₂O / ethanol; H₂O / 1 h / Heating

2: 61 percent / NaH, CuBr*Me₂S / nitrobenzene / 7 h / 110 °C

3: 75 percent / t-BuOK / CH₂Cl₂ / 2 h / -60 °C

4: 98 percent / H₂ / 10percent Pd-C / methanol / 10 h / 25 °C

5: 86 percent / DMAP, pyridine / CH₂Cl₂ / 3 h / 0 °C

With pyridine; chromium(VI) oxide; dmap; copper(I) bromide dimethylsulfide complex; sulfuric acid; potassium tert-butylate; hydrogen; acetic anhydride; sodium hydride; palladium on activated charcoal; In methanol; ethanol; dichloromethane; water; nitrobenzene;

DOI:10.1016/S0040-4039(00)61289-3

Reference yield:

3-bromo-4-nitrobenzaldehyde (101682-68-2) → 3-{3-[4-((S)-2-Acetylamino-2-methoxycarbonyl-ethyl)-phenoxy]-4-benzyloxycarbonylamino-phenyl}-2-tert-butoxycarbonylamino-propionic acid ethyl ester (144333-47-1,144333-48-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 61 percent / NaH, CuBr*Me₂S / nitrobenzene / 7 h / 110 °C

2: 75 percent / t-BuOK / CH₂Cl₂ / 2 h / -60 °C

3: 98 percent / H₂ / 10percent Pd-C / methanol / 10 h / 25 °C

4: 86 percent / DMAP, pyridine / CH₂Cl₂ / 3 h / 0 °C

With pyridine; dmap; copper(I) bromide dimethylsulfide complex; potassium tert-butylate; hydrogen; sodium hydride; palladium on activated charcoal; In methanol; dichloromethane; nitrobenzene;

DOI:10.1016/S0040-4039(00)61289-3

upstream raw materials:

benzyl chloroformate

3-{3-[4-((S)-2-Acetylamino-2-methoxycarbonyl-ethyl)-phenoxy]-4-amino-phenyl}-2-tert-butoxycarbonylamino-propionic acid ethyl ester

3-bromo-4-nitrotoluene

3-bromo-4-nitrobenzaldehyde

Downstream raw materials:

(S)-2-Acetylamino-3-{4-[2-benzyloxycarbonylamino-5-(2-tert-butoxycarbonylamino-2-ethoxycarbonyl-ethyl)-phenoxy]-phenyl}-propionic acid

(9S,12S,15S)-15-Acetylamino-4-benzyloxycarbonylamino-12-(4-hydroxy-benzyl)-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3⁽²²⁾,4,6,17⁽²¹⁾,18-hexaene-9-carboxylic acid ethyl ester

(S)-2-((S)-2-Acetylamino-3-{4-[2-benzyloxycarbonylamino-5-((S)-2-tert-butoxycarbonylamino-2-ethoxycarbonyl-ethyl)-phenoxy]-phenyl}-propionylamino)-3-(4-hydroxy-phenyl)-propionic acid

(S)-2-((S)-2-Acetylamino-3-{4-[2-benzyloxycarbonylamino-5-((S)-2-tert-butoxycarbonylamino-2-ethoxycarbonyl-ethyl)-phenoxy]-phenyl}-propionylamino)-3-(4-hydroxy-phenyl)-propionic acid pentafluorophenyl ester