tricyclo<3.3.1.1^3,7>dec-2-yl *,S^*)>-3-(1H-indol-3-ylmethyl)-3-methyl-4,9,13-trioxo-6-(phenylmethyl)-14-oxa-2,5,8-triazapentadecanoate

Base Information

• Chemical Name: tricyclo<3.3.1.1^3,7>dec-2-yl *,S^*)>-3-(1H-indol-3-ylmethyl)-3-methyl-4,9,13-trioxo-6-(phenylmethyl)-14-oxa-2,5,8-triazapentadecanoate
• CAS No.: 130406-54-1
• Molecular Formula: C₃₈H₄₈N₄O₆
• Molecular Weight: 656.822

Synonyms:tricyclo<3.3.1.1^3,7>dec-2-yl *,S^*)>-3-(1H-indol-3-ylmethyl)-3-methyl-4,9,13-trioxo-6-(phenylmethyl)-14-oxa-2,5,8-triazapentadecanoate

Chemical Property of tricyclo<3.3.1.1^3,7>dec-2-yl *,S^*)>-3-(1H-indol-3-ylmethyl)-3-methyl-4,9,13-trioxo-6-(phenylmethyl)-14-oxa-2,5,8-triazapentadecanoate

Chemical Property:

Purity/Quality:

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Technology Process of tricyclo<3.3.1.1^3,7>dec-2-yl *,S^*)>-3-(1H-indol-3-ylmethyl)-3-methyl-4,9,13-trioxo-6-(phenylmethyl)-14-oxa-2,5,8-triazapentadecanoate

There total 9 articles about tricyclo<3.3.1.1^3,7>dec-2-yl *,S^*)>-3-(1H-indol-3-ylmethyl)-3-methyl-4,9,13-trioxo-6-(phenylmethyl)-14-oxa-2,5,8-triazapentadecanoate 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: 69.0%

methyl 4-(chlorocarbonyl)butyrate (1501-26-4) + tricyclo<3.3.1.13,7>dec-2-yl *,S*)>-<2-<<1-(aminomethyl)-2-phenylethyl>amino>-1-(1H-indol-3-ylmethyl)-1-methyl-2-oxoethyl>carbamate (130406-52-9) → tricyclo<3.3.1.13,7>dec-2-yl *,S*)>-3-(1H-indol-3-ylmethyl)-3-methyl-4,9,13-trioxo-6-(phenylmethyl)-14-oxa-2,5,8-triazapentadecanoate (130406-54-1)

Guidance literature:

With triethylamine; In ethyl acetate; for 4h; Ambient temperature;

DOI:10.1021/jm00105a062

Reference yield:

1-adamantanol (700-57-2) → tricyclo<3.3.1.13,7>dec-2-yl *,S*)>-3-(1H-indol-3-ylmethyl)-3-methyl-4,9,13-trioxo-6-(phenylmethyl)-14-oxa-2,5,8-triazapentadecanoate (130406-54-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 100 percent / pyridine / CH₂Cl₂ / 2 h / Ambient temperature

2: 89 percent / Et₃N / tetrahydrofuran / 0.25 h

3: 90 percent / LiOH / H₂O; dioxane / 18 h / Ambient temperature

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

5: 95 percent / AcOH, H₂ / 10percent Pd/C / ethanol / 30 °C / 2585.7 Torr

6: 69 percent / Et₃N / ethyl acetate / 4 h / Ambient temperature

With pyridine; lithium hydroxide; 2,3,4,5,6-pentafluorophenol; hydrogen; acetic acid; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; ethyl acetate;

DOI:10.1021/jm00105a062

Reference yield:

(9-fluorenylmethoxycarbonyl)-L-phenylalaninol (129397-83-7) → tricyclo<3.3.1.13,7>dec-2-yl *,S*)>-3-(1H-indol-3-ylmethyl)-3-methyl-4,9,13-trioxo-6-(phenylmethyl)-14-oxa-2,5,8-triazapentadecanoate (130406-54-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 80 percent / HN₃, Ph₃P, (i-PrO₂CN)2 / tetrahydrofuran; toluene / 1 h / Ambient temperature

2: 86 percent / LiOH, H₂O / dioxane / 18 h / Ambient temperature

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

4: 95 percent / AcOH, H₂ / 10percent Pd/C / ethanol / 30 °C / 2585.7 Torr

5: 69 percent / Et₃N / ethyl acetate / 4 h / Ambient temperature

With lithium hydroxide; tris-(2-chloro-ethyl)-amine; di-isopropyl azodicarboxylate; 2,3,4,5,6-pentafluorophenol; water; hydrogen; acetic acid; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; ethanol; ethyl acetate; toluene;

DOI:10.1021/jm00105a062

upstream raw materials:

methyl 4-(chlorocarbonyl)butyrate

tricyclo<3.3.1.1^3,7>dec-2-yl *,S^*)>-<2-<<1-(aminomethyl)-2-phenylethyl>amino>-1-(1H-indol-3-ylmethyl)-1-methyl-2-oxoethyl>carbamate

1-adamantanol

(9-fluorenylmethoxycarbonyl)-L-phenylalaninol

Downstream raw materials:

*,S^*)>-5-<<2-<<3-(1H-indol-3-yl)-2-methyl-1-oxo-2-<<(tricyclo<3.3.1.1^3,7>dec-2-yloxy)carbonyl>amino>propyl>amino>-3-phenylpropyl>amino>-5-oxopentanoic acid

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