L-Tyrosine, N-acetyl-O-[5-[2-[[(1,1-dimethylethoxy)carbonyl]amino]-3-ethoxy-3-oxo- 1-propenyl]-2-nitrophenyl]-, methyl ester, (E)-

Base Information

• Chemical Name: L-Tyrosine, N-acetyl-O-[5-[2-[[(1,1-dimethylethoxy)carbonyl]amino]-3-ethoxy-3-oxo- 1-propenyl]-2-nitrophenyl]-, methyl ester, (E)-
• CAS No.: 144333-36-8
• Molecular Formula: C₂₈H₃₃N₃O₁₀
• Molecular Weight: 571.584
• Mol file: 144333-36-8.mol

Synonyms:

Chemical Property of L-Tyrosine, N-acetyl-O-[5-[2-[[(1,1-dimethylethoxy)carbonyl]amino]-3-ethoxy-3-oxo- 1-propenyl]-2-nitrophenyl]-, methyl ester, (E)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of L-Tyrosine, N-acetyl-O-[5-[2-[[(1,1-dimethylethoxy)carbonyl]amino]-3-ethoxy-3-oxo- 1-propenyl]-2-nitrophenyl]-, methyl ester, (E)-

There total 5 articles about L-Tyrosine, N-acetyl-O-[5-[2-[[(1,1-dimethylethoxy)carbonyl]amino]-3-ethoxy-3-oxo- 1-propenyl]-2-nitrophenyl]-, methyl ester, (E)- 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: 75.0%

2-(tert-Butyloxycarbonylamino)-2-(diethoxyphosphoryl)essigsaeure-ethylester (83027-00-3) + (S)-2-Acetylamino-3-[4-(5-formyl-2-nitro-phenoxy)-phenyl]-propionic acid methyl ester (144333-35-7) → (E)-3-{3-[4-((S)-2-Acetylamino-2-methoxycarbonyl-ethyl)-phenoxy]-4-nitro-phenyl}-2-tert-butoxycarbonylamino-acrylic acid ethyl ester (144333-36-8,144333-46-0)

Guidance literature:

With potassium tert-butylate; In dichloromethane; at -60 ℃; for 2h;

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

Reference yield:

2-bromo-p-toluidine (583-68-6) → (E)-3-{3-[4-((S)-2-Acetylamino-2-methoxycarbonyl-ethyl)-phenoxy]-4-nitro-phenyl}-2-tert-butoxycarbonylamino-acrylic acid ethyl ester (144333-36-8,144333-46-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) conc. H₂SO₄, NaNO₂, 2.) NaNO₂, NaHCO₃

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

3: 61 percent / NaH, CuBr*Me₂S / nitrobenzene / 7 h / 110 °C

4: 75 percent / t-BuOK / CH₂Cl₂ / 2 h / -60 °C

With chromium(VI) oxide; copper(I) bromide dimethylsulfide complex; sulfuric acid; potassium tert-butylate; acetic anhydride; sodium hydride; sodium hydrogencarbonate; sodium nitrite; In ethanol; dichloromethane; water; nitrobenzene;

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

Reference yield:

3-bromo-4-nitrotoluene (40385-54-4) → (E)-3-{3-[4-((S)-2-Acetylamino-2-methoxycarbonyl-ethyl)-phenoxy]-4-nitro-phenyl}-2-tert-butoxycarbonylamino-acrylic acid ethyl ester (144333-36-8,144333-46-0)

Guidance literature:

Multi-step reaction with 3 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

With chromium(VI) oxide; copper(I) bromide dimethylsulfide complex; sulfuric acid; potassium tert-butylate; acetic anhydride; sodium hydride; In ethanol; dichloromethane; water; nitrobenzene;

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

upstream raw materials:

2-(tert-Butyloxycarbonylamino)-2-(diethoxyphosphoryl)essigsaeure-ethylester

(S)-2-Acetylamino-3-[4-(5-formyl-2-nitro-phenoxy)-phenyl]-propionic acid methyl ester

2-bromo-p-toluidine

3-bromo-4-nitrotoluene

Downstream raw materials:

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

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

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

(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