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

Base Information

• Chemical Name: tricyclo<3.3.1.1^3,7>dec-2-yl -<2-<<1-(hydroxymethyl)-2-phenylethyl>amino>-1-(1H-indol-3-ylmethyl)-2-thioxoethyl>carbamate
• CAS No.: 139657-21-9
• Molecular Formula: C₃₁H₃₇N₃O₃S
• Molecular Weight: 531.719

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

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

Chemical Property:

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

There total 6 articles about tricyclo<3.3.1.1^3,7>dec-2-yl -<2-<<1-(hydroxymethyl)-2-phenylethyl>amino>-1-(1H-indol-3-ylmethyl)-2-thioxoethyl>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: 70.0%

(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) → tricyclo<3.3.1.13,7>dec-2-yl -<2-<<1-(hydroxymethyl)-2-phenylethyl>amino>-1-(1H-indol-3-ylmethyl)-2-thioxoethyl>carbamate (139657-21-9)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 0.166667h;

DOI:10.1021/jm00086a017

Reference yield:

methyl (2S)-2-amino-3-phenylpropanoate (2577-90-4) → tricyclo<3.3.1.13,7>dec-2-yl -<2-<<1-(hydroxymethyl)-2-phenylethyl>amino>-1-(1H-indol-3-ylmethyl)-2-thioxoethyl>carbamate (139657-21-9)

Guidance literature:

Multi-step reaction with 3 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

3: 70 percent / lithium aluminum hydride / tetrahydrofuran / 0.17 h

With lithium aluminium tetrahydride; 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) → tricyclo<3.3.1.13,7>dec-2-yl -<2-<<1-(hydroxymethyl)-2-phenylethyl>amino>-1-(1H-indol-3-ylmethyl)-2-thioxoethyl>carbamate (139657-21-9)

Guidance literature:

Multi-step reaction with 4 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

4: 70 percent / lithium aluminum hydride / tetrahydrofuran / 0.17 h

With sodium hydroxide; lithium aluminium tetrahydride; 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:

(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

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

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