(E)-3-{(S)-2-[(R)-3-(1H-Indol-3-yl)-2-methyl-2-((1S,2S)-2-methyl-cyclohexyloxycarbonylamino)-propionylamino]-3-phenyl-propylcarbamoyl}-acrylic acid methyl ester

Base Information

• Chemical Name: (E)-3-{(S)-2-[(R)-3-(1H-Indol-3-yl)-2-methyl-2-((1S,2S)-2-methyl-cyclohexyloxycarbonylamino)-propionylamino]-3-phenyl-propylcarbamoyl}-acrylic acid methyl ester
• CAS No.: 146516-46-3
• Molecular Formula: C₃₄H₄₂N₄O₆
• Molecular Weight: 602.731
• Mol file: 146516-46-3.mol

Synonyms:(E)-3-{(S)-2-[(R)-3-(1H-Indol-3-yl)-2-methyl-2-((1S,2S)-2-methyl-cyclohexyloxycarbonylamino)-propionylamino]-3-phenyl-propylcarbamoyl}-acrylic acid methyl ester

Chemical Property of (E)-3-{(S)-2-[(R)-3-(1H-Indol-3-yl)-2-methyl-2-((1S,2S)-2-methyl-cyclohexyloxycarbonylamino)-propionylamino]-3-phenyl-propylcarbamoyl}-acrylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-3-{(S)-2-[(R)-3-(1H-Indol-3-yl)-2-methyl-2-((1S,2S)-2-methyl-cyclohexyloxycarbonylamino)-propionylamino]-3-phenyl-propylcarbamoyl}-acrylic acid methyl ester

There total 6 articles about (E)-3-{(S)-2-[(R)-3-(1H-Indol-3-yl)-2-methyl-2-((1S,2S)-2-methyl-cyclohexyloxycarbonylamino)-propionylamino]-3-phenyl-propylcarbamoyl}-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: 56.0%

methyl pentafluorophenyl fumarate + [(R)-1-((S)-1-Aminomethyl-2-phenyl-ethylcarbamoyl)-2-(1H-indol-3-yl)-1-methyl-ethyl]-carbamic acid (1S,2S)-2-methyl-cyclohexyl ester (146516-45-2) → (E)-3-{(S)-2-[(R)-3-(1H-Indol-3-yl)-2-methyl-2-((1S,2S)-2-methyl-cyclohexyloxycarbonylamino)-propionylamino]-3-phenyl-propylcarbamoyl}-acrylic acid methyl ester (146516-46-3)

Guidance literature:

In ethyl acetate; for 16h; Ambient temperature;

DOI:10.1021/jm00057a005

Reference yield:

trans-2-methylcyclohexanol (15963-37-8) → (E)-3-{(S)-2-[(R)-3-(1H-Indol-3-yl)-2-methyl-2-((1S,2S)-2-methyl-cyclohexyloxycarbonylamino)-propionylamino]-3-phenyl-propylcarbamoyl}-acrylic acid methyl ester (146516-46-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) pyridine, 2.) Et₃N / 1.) CH₂Cl₂, 0 deg C, 1 h, 2.) THF, RT, 3 h

2: 96 percent / aq. LiOH / dioxane / 36 h / Ambient temperature

3: 1.) pentafluorophenyl, N,N'-dicyclohexylcarbodiimide / 1.) EtOAc, 0 deg C, 4 h, 2.) EtOAc, RT, 18 h

4: 100 percent / 1percent ethanolic AcOH, H₂ / 10percent Pd/C / 2 h / 30 °C / 2585.7 Torr

5: 56 percent / ethyl acetate / 16 h / Ambient temperature

With pyridine; lithium hydroxide; Pentafluorobenzene; hydrogen; acetic acid; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In 1,4-dioxane; ethyl acetate;

DOI:10.1021/jm00057a005

Reference yield:

α-methyl-(R)-tryptophan methyl ester (96551-27-8) → (E)-3-{(S)-2-[(R)-3-(1H-Indol-3-yl)-2-methyl-2-((1S,2S)-2-methyl-cyclohexyloxycarbonylamino)-propionylamino]-3-phenyl-propylcarbamoyl}-acrylic acid methyl ester (146516-46-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) pyridine, 2.) Et₃N / 1.) CH₂Cl₂, 0 deg C, 1 h, 2.) THF, RT, 3 h

2: 96 percent / aq. LiOH / dioxane / 36 h / Ambient temperature

3: 1.) pentafluorophenyl, N,N'-dicyclohexylcarbodiimide / 1.) EtOAc, 0 deg C, 4 h, 2.) EtOAc, RT, 18 h

4: 100 percent / 1percent ethanolic AcOH, H₂ / 10percent Pd/C / 2 h / 30 °C / 2585.7 Torr

5: 56 percent / ethyl acetate / 16 h / Ambient temperature

With pyridine; lithium hydroxide; Pentafluorobenzene; hydrogen; acetic acid; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In 1,4-dioxane; ethyl acetate;

DOI:10.1021/jm00057a005

upstream raw materials:

[(R)-1-((S)-1-Aminomethyl-2-phenyl-ethylcarbamoyl)-2-(1H-indol-3-yl)-1-methyl-ethyl]-carbamic acid (1S,2S)-2-methyl-cyclohexyl ester

trans-2-methylcyclohexanol

α-methyl-(R)-tryptophan methyl ester

carbamic acid, <1S-<1α,2β>>-<2-<<1-(azidomethyl)-2-phenylethyl>amino>-1-(1H-indol-3-ylmethyl)-1-methyl-2-oxoethyl>-, 2-methylcyclohexyl ester