tricyclo[3.3.1.1^3,7]dec-2-yl (R)-{1-(1H-indol-3-ylmethyl)-1-methyl-2-oxo-2-[(2-phenylethyl)amino]ethyl}carbamate

Base Information

• Chemical Name: tricyclo[3.3.1.1^3,7]dec-2-yl (R)-{1-(1H-indol-3-ylmethyl)-1-methyl-2-oxo-2-[(2-phenylethyl)amino]ethyl}carbamate
• CAS No.: 130406-43-8
• Molecular Formula: C₃₁H₃₇N₃O₃
• Molecular Weight: 499.653

Synonyms:tricyclo[3.3.1.1^3,7]dec-2-yl (R)-{1-(1H-indol-3-ylmethyl)-1-methyl-2-oxo-2-[(2-phenylethyl)amino]ethyl}carbamate

Chemical Property of tricyclo[3.3.1.1^3,7]dec-2-yl (R)-{1-(1H-indol-3-ylmethyl)-1-methyl-2-oxo-2-[(2-phenylethyl)amino]ethyl}carbamate

Chemical Property:

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Technology Process of tricyclo[3.3.1.1^3,7]dec-2-yl (R)-{1-(1H-indol-3-ylmethyl)-1-methyl-2-oxo-2-[(2-phenylethyl)amino]ethyl}carbamate

There total 3 articles about tricyclo[3.3.1.1^3,7]dec-2-yl (R)-{1-(1H-indol-3-ylmethyl)-1-methyl-2-oxo-2-[(2-phenylethyl)amino]ethyl}carbamate 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:

1-adamantanol (700-57-2) → tricyclo[3.3.1.13,7]dec-2-yl (R)-{1-(1H-indol-3-ylmethyl)-1-methyl-2-oxo-2-[(2-phenylethyl)amino]ethyl}carbamate (130406-43-8)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / CH₂Cl₂ / 1 h / Ambient temperature

2: triethylamine / tetrahydrofuran / 4 h / Ambient temperature

With pyridine; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/0223-5234(93)90077-R

Reference yield:

N-[(2-adamantyloxy) carbonyl]-α-methyl-D-tryptophan methyl ester (130406-39-2) → tricyclo[3.3.1.13,7]dec-2-yl (R)-{1-(1H-indol-3-ylmethyl)-1-methyl-2-oxo-2-[(2-phenylethyl)amino]ethyl}carbamate (130406-43-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / LiOH / H₂O; dioxane / 18 h / Ambient temperature

2: 1.) C₆F₅OH, N,N'-dicyclohexylcarbodiimide / 1.) EtOAc, 0 deg C, 18 h, 2.) 48 h

With lithium hydroxide; 2,3,4,5,6-pentafluorophenol; dicyclohexyl-carbodiimide; In 1,4-dioxane; water;

DOI:10.1021/jm00105a062

Reference yield:

2-adamantyl chloroformate (53120-53-9) + R-α-methyl-tryptophanyl-2-phenethylamide → tricyclo[3.3.1.13,7]dec-2-yl (R)-{1-(1H-indol-3-ylmethyl)-1-methyl-2-oxo-2-[(2-phenylethyl)amino]ethyl}carbamate (130406-43-8)

Guidance literature:

With triethylamine; In tetrahydrofuran; for 4h; Yield given; Ambient temperature;

DOI:10.1016/0223-5234(93)90077-R

upstream raw materials:

2-adamantyl chloroformate

1-adamantanol

N-[(2-adamantyloxy) carbonyl]-α-methyl-D-tryptophan methyl ester

Downstream raw materials:

ethyl (R)-7-<<3-(1H-indol-3-yl)-2-methyl-2-<<(tricyclo<3.3.1.1^3,7>dec-2-yloxy)carbonyl>amino>propyl>(2-phenylethyl)amino>-7-oxoheptanoate

ethyl (R)-4-<<3-(1H-indol-3-yl)-2-methyl-2-<<(tricyclo<3.3.1.1^3,7>dec-2-yloxy)carbonyl>amino>propyl>(2-phenylethyl)amino>-4-oxobutanoate

(R)-4-<<3-(1H-indol-3-yl)-2-methyl-2-<<(tricyclo<3.3.1.1^3,7>dec-2-yloxy)carbonyl>amino>propyl>(2-phenylethyl)amino>-4-oxobutanoic acid

tricyclo<3.3.1.1^3,7>dec-2-yl -<2--1-(1H-indol-3-ylmethyl)-1-methylethyl>carbamate

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