methyl (Z)-2-({(2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanoyl}-amino)-3-phenyl-2-propenoate

Base Information

• Chemical Name: methyl (Z)-2-({(2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanoyl}-amino)-3-phenyl-2-propenoate
• CAS No.: 97512-72-6
• Molecular Formula: C₂₄H₂₈N₂O₅
• Molecular Weight: 424.497
• Mol file: 97512-72-6.mol

Synonyms:methyl (Z)-2-({(2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanoyl}-amino)-3-phenyl-2-propenoate

Chemical Property of methyl (Z)-2-({(2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanoyl}-amino)-3-phenyl-2-propenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (Z)-2-({(2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanoyl}-amino)-3-phenyl-2-propenoate

There total 6 articles about methyl (Z)-2-({(2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanoyl}-amino)-3-phenyl-2-propenoate 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: 84.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + (Z)-Boc-Phe-ΔPhe (97510-44-6) → methyl (Z)-2-({(2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanoyl}-amino)-3-phenyl-2-propenoate (97512-72-6)

Guidance literature:

In methanol; diethyl ether;

Reference yield: 58.0%

iodobenzene (591-50-4) + methyl 2-({(2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanoyl}-amino)-acrylate (79807-13-9) → methyl (Z)-2-({(2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanoyl}-amino)-3-phenyl-2-propenoate (97512-72-6)

Guidance literature:

With tetrabutylammomium bromide; potassium acetate; palladium diacetate; In N,N-dimethyl-formamide; at 95 ℃; for 18h;

DOI:10.1081/SCC-200054757

Reference yield:

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → methyl (Z)-2-({(2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanoyl}-amino)-3-phenyl-2-propenoate (97512-72-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 82 percent / 4-methylmorpholine; 1-hydroxybenzotriazole; dicyclohexyl carbodiimide / CH₂Cl₂ / 7.5 h / 0 - 20 °C

2: 78 percent / methanesulfonyl chloride; triethylamine / CH₂Cl₂ / 3 h / 0 - 20 °C

3: 58 percent / n-Bu₄NBr; potassium acetate / Pd(OAc)2 / dimethylformamide / 18 h / 95 °C

With 4-methyl-morpholine; tetrabutylammomium bromide; potassium acetate; benzotriazol-1-ol; methanesulfonyl chloride; triethylamine; dicyclohexyl-carbodiimide; palladium diacetate; In dichloromethane; N,N-dimethyl-formamide; 3: Heck arylation;

DOI:10.1081/SCC-200054757

upstream raw materials:

diazomethane

(Z)-Boc-Phe-ΔPhe

methanol

N-tert-butoxycarbonyl-L-phenylalanine

Downstream raw materials:

Boc-L-Phe-Z-ΔPhe(β-I)-OMe

Boc-L-Phe-E-ΔPhe(β-Br)-OMe

Boc-L-Phe-Z-ΔPhe(β-Br)-OMe

Refernces

• 1、 Torino, Domenica,Mollica, Adriano,Pinnen, Francesco,Feliciani, Federica,Lucente, Gino,Fabrizi, Giancarlo,Portalone, Gustavo,Davis, Peg,Lai, Josephine,Ma, Shou-Wu,Porreca, Frank,Hruby, Victor J.. "Synthesis and evaluation of new endomorphin-2 analogues containing (Z)-α,β-didehydrophenylalanine (δZPhe) residues". supporting information; experimental part. p. 4550 - 4554. Retrieved 2010/08/06.
• 2、 Shin, Chuung-gi,Yonezawa, Yasuchika,Ikeda, Masahiro. "Dehydrooligopeptides. VII. Convenient Synthesis of Various Dehydrodi- and tripeptide Esters by Using N-Carboxy α-Dehydroamino Acid Anhydride". . p. 3573 - 3579. Retrieved 2007/10/02.