(Z)-3-(3-Bromo-phenyl)-2-tert-butoxycarbonylamino-acrylic acid methyl ester

Base Information

• Chemical Name: (Z)-3-(3-Bromo-phenyl)-2-tert-butoxycarbonylamino-acrylic acid methyl ester
• CAS No.: 218927-23-2
• Molecular Formula: C₁₅H₁₈BrNO₄
• Molecular Weight: 356.216
• Mol file: 218927-23-2.mol

Synonyms:(Z)-3-(3-Bromo-phenyl)-2-tert-butoxycarbonylamino-acrylic acid methyl ester

Chemical Property of (Z)-3-(3-Bromo-phenyl)-2-tert-butoxycarbonylamino-acrylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-3-(3-Bromo-phenyl)-2-tert-butoxycarbonylamino-acrylic acid methyl ester

There total 1 articles about (Z)-3-(3-Bromo-phenyl)-2-tert-butoxycarbonylamino-acrylic acid methyl 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: 63.0%

1-Bromo-3-iodobenzene (591-18-4) + methyl 2-[(tert-butoxycarbonyl)amino]acrylate (55477-80-0) → (Z)-3-(3-Bromo-phenyl)-2-tert-butoxycarbonylamino-acrylic acid methyl ester (218927-23-2)

Guidance literature:

With tetrabutyl-ammonium chloride; sodium hydrogencarbonate; hydroquinone; palladium diacetate; In N,N-dimethyl-formamide; at 60 ℃; for 18h;

DOI:10.1039/a805350b

Reference yield: 57.0%

2-acetylamino-acrylic acid benzyl ester (73908-43-7) + (Z)-3-(3-Bromo-phenyl)-2-tert-butoxycarbonylamino-acrylic acid methyl ester (218927-23-2) → (Z)-2-Acetylamino-3-[3-((Z)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-vinyl)-phenyl]-acrylic acid benzyl ester (218927-25-4)

Guidance literature:

With tetrabutyl-ammonium chloride; sodium hydrogencarbonate; hydroquinone; palladium diacetate; In N,N-dimethyl-formamide; at 85 ℃;

DOI:10.1039/a805350b

Reference yield:

(Z)-3-(3-Bromo-phenyl)-2-tert-butoxycarbonylamino-acrylic acid methyl ester (218927-23-2) → (S)-3-{3-[(S)-2-Acetylamino-2-(2-carboxy-ethylcarbamoyl)-ethyl]-phenyl}-2-amino-propionic acid methyl ester

Guidance literature:

Multi-step reaction with 5 steps

1: 57 percent / NaHCO₃, Bu₄NCl, hydroquinone / Pd(OAc)2 / dimethylformamide / 85 °C

2: 98 percent / H₂ / >⁽¹⁺⁾*OTf^(1-) / methanol / 6 h / 2068.6 Torr / Ambient temperature

3: H₂ / 5percent Pd/C / ethanol / 3 h / Ambient temperature

4: 74 percent / DIEA, HOBt*H₂O, DCC / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) r.t., 16 h

5: TFA / 2 h / Ambient temperature

With tetrabutyl-ammonium chloride; hydrogen; sodium hydrogencarbonate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; hydroquinone; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium diacetate; palladium on activated charcoal; benzene; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide;

DOI:10.1039/a805350b

upstream raw materials:

1-Bromo-3-iodobenzene

methyl 2-[(tert-butoxycarbonyl)amino]acrylate

Downstream raw materials:

(Z)-2-Acetylamino-3-[3-((Z)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-vinyl)-phenyl]-acrylic acid benzyl ester

(S)-2-Acetylamino-3-{3-[(S)-2-(2-amino-acetylamino)-2-methoxycarbonyl-ethyl]-phenyl}-propionic acid

(S)-2-Acetylamino-3-{3-[(S)-2-(4-amino-butyrylamino)-2-methoxycarbonyl-ethyl]-phenyl}-propionic acid

(S)-2-Acetylamino-3-{3-[(S)-2-(5-amino-pentanoylamino)-2-methoxycarbonyl-ethyl]-phenyl}-propionic acid