ethyl -4-<<2-<<2-<<(1,1-dimethylethoxy)carbonyl>amino>-2-phenylethyl>amino>-1-(1H-indol-3-ylmethyl)-1-methyl-2-oxoethyl>amino>-4-oxobutanoate

Base Information

• Chemical Name: ethyl -4-<<2-<<2-<<(1,1-dimethylethoxy)carbonyl>amino>-2-phenylethyl>amino>-1-(1H-indol-3-ylmethyl)-1-methyl-2-oxoethyl>amino>-4-oxobutanoate
• CAS No.: 146953-12-0
• Molecular Formula: C₃₁H₄₀N₄O₆
• Molecular Weight: 564.682
• Mol file: 146953-12-0.mol

Synonyms:ethyl -4-<<2-<<2-<<(1,1-dimethylethoxy)carbonyl>amino>-2-phenylethyl>amino>-1-(1H-indol-3-ylmethyl)-1-methyl-2-oxoethyl>amino>-4-oxobutanoate

Chemical Property of ethyl -4-<<2-<<2-<<(1,1-dimethylethoxy)carbonyl>amino>-2-phenylethyl>amino>-1-(1H-indol-3-ylmethyl)-1-methyl-2-oxoethyl>amino>-4-oxobutanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl -4-<<2-<<2-<<(1,1-dimethylethoxy)carbonyl>amino>-2-phenylethyl>amino>-1-(1H-indol-3-ylmethyl)-1-methyl-2-oxoethyl>amino>-4-oxobutanoate

There total 5 articles about ethyl -4-<<2-<<2-<<(1,1-dimethylethoxy)carbonyl>amino>-2-phenylethyl>amino>-1-(1H-indol-3-ylmethyl)-1-methyl-2-oxoethyl>amino>-4-oxobutanoate 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: 93.0%

ethyl 3-(chloroformyl)propionate (14794-31-1,97900-84-0) + 1,1-dimethylethyl -<2-<<2-amino-3-(1H-indol-3-yl)-2-methyl-1-oxopropyl>amino>-1-phenylethyl>carbamate (146953-11-9) → ethyl -4-<<2-<<2-<<(1,1-dimethylethoxy)carbonyl>amino>-2-phenylethyl>amino>-1-(1H-indol-3-ylmethyl)-1-methyl-2-oxoethyl>amino>-4-oxobutanoate (146953-12-0)

Guidance literature:

With triethylamine; In tetrahydrofuran; for 2h; Ambient temperature;

DOI:10.1016/S0040-4020(01)86257-8

Reference yield:

α-methyl-(R)-tryptophan methyl ester (96551-27-8) → ethyl -4-<<2-<<2-<<(1,1-dimethylethoxy)carbonyl>amino>-2-phenylethyl>amino>-1-(1H-indol-3-ylmethyl)-1-methyl-2-oxoethyl>amino>-4-oxobutanoate (146953-12-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 84 percent / Et₃N / tetrahydrofuran / 1 h / Ambient temperature

2: 99 percent / LiOH / dioxane; H₂O / 24 h / Ambient temperature

3: 1) 1-hydroxy-1H-benzotriazole, dicyclohexyl carbodiimide, 2) Et₃N / 1) ethyl acetate, rt, 2 h, 2) overnight

4: 98 percent / H₂ / 20percent Pd/C / methanol / 4 h

5: 93 percent / Et₃N / tetrahydrofuran / 2 h / Ambient temperature

With lithium hydroxide; hydrogen; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; water;

DOI:10.1016/S0040-4020(01)86257-8

Reference yield:

α-methyl-N-<(phenylmethoxy)carbonyl>-D-tryptophan (146953-09-5) → ethyl -4-<<2-<<2-<<(1,1-dimethylethoxy)carbonyl>amino>-2-phenylethyl>amino>-1-(1H-indol-3-ylmethyl)-1-methyl-2-oxoethyl>amino>-4-oxobutanoate (146953-12-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) 1-hydroxy-1H-benzotriazole, dicyclohexyl carbodiimide, 2) Et₃N / 1) ethyl acetate, rt, 2 h, 2) overnight

2: 98 percent / H₂ / 20percent Pd/C / methanol / 4 h

3: 93 percent / Et₃N / tetrahydrofuran / 2 h / Ambient temperature

With hydrogen; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol;

DOI:10.1016/S0040-4020(01)86257-8

upstream raw materials:

ethyl 3-(chloroformyl)propionate

1,1-dimethylethyl -<2-<<2-amino-3-(1H-indol-3-yl)-2-methyl-1-oxopropyl>amino>-1-phenylethyl>carbamate

α-methyl-(R)-tryptophan methyl ester

α-methyl-N-<(phenylmethoxy)carbonyl>-D-tryptophan

Downstream raw materials:

-4-<<2-<(2-amino-2-phenylethyl)amino>-1-(1H-indol-3-ylmethyl)-1-methyl-2-oxoethyl>amino>-4-oxobutanoic acid monohydrochloride

-4-<<2-<<2-<<(1,1-dimethylethoxy)carbonyl>amino>-2-phenylethyl>amino>-1-(1H-indol-3-ylmethyl)-1-methyl-2-oxoethyl>amino>-4-oxobutanoic acid