(R)-N-<3-(1H-indol-3-yl)-1-thioxo-2-<<(tricyclo<3.3.1.1^3,7>dec-2-yloxy)carbonyl>amino>propyl>-(S)-phenylalanine methyl ester

Base Information

• Chemical Name: (R)-N-<3-(1H-indol-3-yl)-1-thioxo-2-<<(tricyclo<3.3.1.1^3,7>dec-2-yloxy)carbonyl>amino>propyl>-(S)-phenylalanine methyl ester
• CAS No.: 139657-20-8
• Molecular Formula: C₃₂H₃₇N₃O₄S
• Molecular Weight: 559.729

Synonyms:(R)-N-<3-(1H-indol-3-yl)-1-thioxo-2-<<(tricyclo<3.3.1.1^3,7>dec-2-yloxy)carbonyl>amino>propyl>-(S)-phenylalanine methyl ester

Chemical Property of (R)-N-<3-(1H-indol-3-yl)-1-thioxo-2-<<(tricyclo<3.3.1.1^3,7>dec-2-yloxy)carbonyl>amino>propyl>-(S)-phenylalanine methyl ester

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Technology Process of (R)-N-<3-(1H-indol-3-yl)-1-thioxo-2-<<(tricyclo<3.3.1.1^3,7>dec-2-yloxy)carbonyl>amino>propyl>-(S)-phenylalanine methyl ester

There total 5 articles about (R)-N-<3-(1H-indol-3-yl)-1-thioxo-2-<<(tricyclo<3.3.1.1^3,7>dec-2-yloxy)carbonyl>amino>propyl>-(S)-phenylalanine 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: 71.0%

N-3,7>dec-2-yloxy)carbonyl>-(R)-tryptophyl>-(S)-phenylalanine methyl ester (139657-19-5) → (R)-N-<3-(1H-indol-3-yl)-1-thioxo-2-<<(tricyclo<3.3.1.13,7>dec-2-yloxy)carbonyl>amino>propyl>-(S)-phenylalanine methyl ester (139657-20-8)

Guidance literature:

With 2,4-bis(phenylthio)-1,3-dithia-2λ⁵,4λ⁵-diphosphetane 2,4-disulphide; In tetrahydrofuran; for 18h; Ambient temperature;

DOI:10.1021/jm00086a017

Reference yield:

methyl (2S)-2-amino-3-phenylpropanoate (2577-90-4) → (R)-N-<3-(1H-indol-3-yl)-1-thioxo-2-<<(tricyclo<3.3.1.13,7>dec-2-yloxy)carbonyl>amino>propyl>-(S)-phenylalanine methyl ester (139657-20-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) N,N'-dicyclohexylcarbodiimide, 1-hydroxybenzotriazole monohydrate (HOBt) / 1.) CH₂Cl₂, 10 min, 2.) CH₂Cl₂, ethyl acetate, RT, 2 h

2: 71 percent / 2,4-bis(phenylthio)-1,3-dithia-2,4-diphosphetane-2,4-disulfide / tetrahydrofuran / 18 h / Ambient temperature

With 2,4-bis(phenylthio)-1,3-dithia-2λ⁵,4λ⁵-diphosphetane 2,4-disulphide; 1-hydroxybenzotriazol-hydrate; dicyclohexyl-carbodiimide; In tetrahydrofuran;

DOI:10.1021/jm00086a017

Reference yield:

2-adamantyl chloroformate (53120-53-9) → (R)-N-<3-(1H-indol-3-yl)-1-thioxo-2-<<(tricyclo<3.3.1.13,7>dec-2-yloxy)carbonyl>amino>propyl>-(S)-phenylalanine methyl ester (139657-20-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 51 percent / NaHCO₃, NaOH / dioxane / 18 h / Ambient temperature

2: 1.) N,N'-dicyclohexylcarbodiimide, 1-hydroxybenzotriazole monohydrate (HOBt) / 1.) CH₂Cl₂, 10 min, 2.) CH₂Cl₂, ethyl acetate, RT, 2 h

3: 71 percent / 2,4-bis(phenylthio)-1,3-dithia-2,4-diphosphetane-2,4-disulfide / tetrahydrofuran / 18 h / Ambient temperature

With sodium hydroxide; sodium hydrogencarbonate; 2,4-bis(phenylthio)-1,3-dithia-2λ⁵,4λ⁵-diphosphetane 2,4-disulphide; 1-hydroxybenzotriazol-hydrate; dicyclohexyl-carbodiimide; In tetrahydrofuran; 1,4-dioxane;

DOI:10.1021/jm00086a017

upstream raw materials:

N-3,7>dec-2-yloxy)carbonyl>-(R)-tryptophyl>-(S)-phenylalanine methyl ester

methyl (2S)-2-amino-3-phenylpropanoate

2-adamantyl chloroformate

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

Downstream raw materials:

tricyclo<3.3.1.1^3,7>dec-2-yl -<2-<<1-(hydroxymethyl)-2-phenylethyl>amino>-1-(1H-indol-3-ylmethyl)-2-thioxoethyl>carbamate

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