4-{(1E)-3-[6,7-dimethoxy-3-(4-methoxyphenyl)-2-oxoquinolin-1(2H)-yl]prop-1-enyl}-N-[(1,1-dimethylethoxy)carbonyl]phenylalanine

Base Information

• Chemical Name: 4-{(1E)-3-[6,7-dimethoxy-3-(4-methoxyphenyl)-2-oxoquinolin-1(2H)-yl]prop-1-enyl}-N-[(1,1-dimethylethoxy)carbonyl]phenylalanine
• CAS No.: 874184-03-9
• Molecular Formula: C₃₅H₃₈N₂O₈
• Molecular Weight: 614.695
• Mol file: 874184-03-9.mol

Synonyms:4-{(1E)-3-[6,7-dimethoxy-3-(4-methoxyphenyl)-2-oxoquinolin-1(2H)-yl]prop-1-enyl}-N-[(1,1-dimethylethoxy)carbonyl]phenylalanine

Chemical Property of 4-{(1E)-3-[6,7-dimethoxy-3-(4-methoxyphenyl)-2-oxoquinolin-1(2H)-yl]prop-1-enyl}-N-[(1,1-dimethylethoxy)carbonyl]phenylalanine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-{(1E)-3-[6,7-dimethoxy-3-(4-methoxyphenyl)-2-oxoquinolin-1(2H)-yl]prop-1-enyl}-N-[(1,1-dimethylethoxy)carbonyl]phenylalanine

There total 2 articles about 4-{(1E)-3-[6,7-dimethoxy-3-(4-methoxyphenyl)-2-oxoquinolin-1(2H)-yl]prop-1-enyl}-N-[(1,1-dimethylethoxy)carbonyl]phenylalanine 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: 90.0%

6,7-dimethoxy-3-(4-methoxyphenyl)-1-(prop-2-en-1-yl)-1H-quinolin-2-one (874183-97-8) + methyl (±)-3-(4-bromophenyl)-2-((tert-butoxycarbonyl)amino)propanoate (132067-41-5) → 4-{(1E)-3-[6,7-dimethoxy-3-(4-methoxyphenyl)-2-oxoquinolin-1(2H)-yl]prop-1-enyl}-N-[(1,1-dimethylethoxy)carbonyl]phenylalanine (874184-03-9)

Guidance literature:

With caesium carbonate; triphenylphosphine; palladium diacetate; In water; N,N-dimethyl-formamide; at 80 ℃; for 10h; microwave irradiation;

DOI:10.1002/hlca.200690275

Reference yield:

6,7-dimethoxy-3-(4-methoxyphenyl)-quinolin-2(1H)-one (68742-15-4) → 4-{(1E)-3-[6,7-dimethoxy-3-(4-methoxyphenyl)-2-oxoquinolin-1(2H)-yl]prop-1-enyl}-N-[(1,1-dimethylethoxy)carbonyl]phenylalanine (874184-03-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C

1.2: 83 percent / tetrahydrofuran; toluene / 0.25 h / 120 °C / 11251.1 Torr / microwave irradiation

2.1: 90 percent / Ph₃P; Cs₂CO₃ / Pd(OAc)2 / H₂O; dimethylformamide / 10 h / 80 °C / microwave irradiation

With potassium hexamethylsilazane; caesium carbonate; triphenylphosphine; palladium diacetate; In tetrahydrofuran; water; N,N-dimethyl-formamide; toluene; 2.1: Heck cross-coupling;

DOI:10.1002/hlca.200690275

Reference yield:

4-{(1E)-3-[6,7-dimethoxy-3-(4-methoxyphenyl)-2-oxoquinolin-1(2H)-yl]prop-1-enyl}-N-[(1,1-dimethylethoxy)carbonyl]phenylalanine (874184-03-9) → 4-{3-[6,7-dimethoxy-3-(4-methoxyphenyl)-2-oxoquinolin-1(2H)-yl]propyl}-N-{[(9H-fluoren-9-yl)methoxy]carbonyl}phenylalanine

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / H₂ / Pd/C / methanol / 16 h / 750.08 Torr

2: CF₃COOH; (i-Pr)3SiH / CH₂Cl₂ / 2 h / 20 °C

3: 0.82 g / aq. Na₂CO₃ / acetone / 4 h

With chlorotriisopropylsilane; hydrogen; sodium carbonate; trifluoroacetic acid; palladium on activated charcoal; In methanol; dichloromethane; acetone;

DOI:10.1002/hlca.200690275

upstream raw materials:

6,7-dimethoxy-3-(4-methoxyphenyl)-1-(prop-2-en-1-yl)-1H-quinolin-2-one

methyl (±)-3-(4-bromophenyl)-2-((tert-butoxycarbonyl)amino)propanoate

6,7-dimethoxy-3-(4-methoxyphenyl)-quinolin-2(1H)-one

Downstream raw materials:

4-{3-[6,7-dimethoxy-3-(4-methoxyphenyl)-2-oxoquinolin-1(2H)-yl]propyl}phenylalanine