L-Tyrosine, N-(2-benzoylphenyl)-O-[2-[2-[3-[3-[[(1,1-dimethylethoxy)carbonyl]amino] -1-propynyl]phenyl]-5-methyl-4-oxazolyl]ethyl]-, methyl ester

Base Information

• Chemical Name: L-Tyrosine, N-(2-benzoylphenyl)-O-[2-[2-[3-[3-[[(1,1-dimethylethoxy)carbonyl]amino] -1-propynyl]phenyl]-5-methyl-4-oxazolyl]ethyl]-, methyl ester
• CAS No.: 679834-89-0
• Molecular Formula: C43H43N3O7
• Molecular Weight: 713.83
• Mol file: 679834-89-0.mol

Synonyms:

Chemical Property of L-Tyrosine, N-(2-benzoylphenyl)-O-[2-[2-[3-[3-[[(1,1-dimethylethoxy)carbonyl]amino] -1-propynyl]phenyl]-5-methyl-4-oxazolyl]ethyl]-, methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of L-Tyrosine, N-(2-benzoylphenyl)-O-[2-[2-[3-[3-[[(1,1-dimethylethoxy)carbonyl]amino] -1-propynyl]phenyl]-5-methyl-4-oxazolyl]ethyl]-, methyl ester

There total 5 articles about L-Tyrosine, N-(2-benzoylphenyl)-O-[2-[2-[3-[3-[[(1,1-dimethylethoxy)carbonyl]amino] -1-propynyl]phenyl]-5-methyl-4-oxazolyl]ethyl]-, 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: 79.0%

N-tert-Butoxycarbonyl-1-amino-3-propyne (92136-39-5) + methyl (2S)-2-[(2-benzoylphenyl)amino]-3-(4-{2-[2-(3-iodophenyl)-5-methyl-1,3-oxazol-4-yl]ethoxy}phenyl)propanoate (679834-87-8) → methyl (2S)-2-[(2-benzoylphenyl)amino]-3-(4-{2-[2-(3-{3-[(tert-butoxycarbonyl)amino]-1-propynyl}phenyl)-5-methyl-1,3-oxazol-4-yl]ethoxy}phenyl)propanoate (679834-89-0)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; at 60 ℃; for 0.5h;

DOI:10.1016/S0968-0896(03)00494-2

Reference yield:

3-iodobenzoyl chloride (1711-10-0) → methyl (2S)-2-[(2-benzoylphenyl)amino]-3-(4-{2-[2-(3-{3-[(tert-butoxycarbonyl)amino]-1-propynyl}phenyl)-5-methyl-1,3-oxazol-4-yl]ethoxy}phenyl)propanoate (679834-89-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 19.2 g / ammonia / tetrahydrofuran / 15 h / -78 - -40 °C

2: 4.2 g / 4 h / 125 °C

3: 87 percent / LiBH₄ / tetrahydrofuran / 1.5 h / 22 - 50 °C

4: 61 percent / diethyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 24 h / 22 °C

5: 79 percent / Pd(PPh₃)2Cl₂; triethylamine; CuI / 0.5 h / 60 °C

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; lithium borohydride; ammonia; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 4: Mitsunobu reaction / 5: Sonagashira coupling;

DOI:10.1016/S0968-0896(03)00494-2

Reference yield:

ethyl 4-bromo-3-oxopentanoate (36187-69-6) → methyl (2S)-2-[(2-benzoylphenyl)amino]-3-(4-{2-[2-(3-{3-[(tert-butoxycarbonyl)amino]-1-propynyl}phenyl)-5-methyl-1,3-oxazol-4-yl]ethoxy}phenyl)propanoate (679834-89-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 4.2 g / 4 h / 125 °C

2: 87 percent / LiBH₄ / tetrahydrofuran / 1.5 h / 22 - 50 °C

3: 61 percent / diethyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 24 h / 22 °C

4: 79 percent / Pd(PPh₃)2Cl₂; triethylamine; CuI / 0.5 h / 60 °C

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; lithium borohydride; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 3: Mitsunobu reaction / 4: Sonagashira coupling;

DOI:10.1016/S0968-0896(03)00494-2

upstream raw materials:

N-tert-Butoxycarbonyl-1-amino-3-propyne

methyl (2S)-2-[(2-benzoylphenyl)amino]-3-(4-{2-[2-(3-iodophenyl)-5-methyl-1,3-oxazol-4-yl]ethoxy}phenyl)propanoate

3-iodobenzoyl chloride

ethyl 4-bromo-3-oxopentanoate

Downstream raw materials:

(2S)-2-[(2-benzoylphenyl)amino]-3-(4-{2-[2-(3-{3-[(tert-butoxycarbonyl)amino]-1-propynyl}phenyl)-5-methyl-1,3-oxazol-4-yl]ethoxy}phenyl)propanoic acid