tricyclo<3.3.1.1^3,7>dec-2-yl *,S^*)>-3-(1H-indol-3-ylmethyl)-3-methyl-4,9,11-trioxo-6-(phenylmethyl)-12-oxa-2,5,8-triazatridecanoate

Base Information

• Chemical Name: tricyclo<3.3.1.1^3,7>dec-2-yl *,S^*)>-3-(1H-indol-3-ylmethyl)-3-methyl-4,9,11-trioxo-6-(phenylmethyl)-12-oxa-2,5,8-triazatridecanoate
• CAS No.: 130406-55-2
• Molecular Formula: C₃₆H₄₄N₄O₆
• Molecular Weight: 628.769

Synonyms:tricyclo<3.3.1.1^3,7>dec-2-yl *,S^*)>-3-(1H-indol-3-ylmethyl)-3-methyl-4,9,11-trioxo-6-(phenylmethyl)-12-oxa-2,5,8-triazatridecanoate

Chemical Property of tricyclo<3.3.1.1^3,7>dec-2-yl *,S^*)>-3-(1H-indol-3-ylmethyl)-3-methyl-4,9,11-trioxo-6-(phenylmethyl)-12-oxa-2,5,8-triazatridecanoate

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-4,9,11-trioxo-6-(phenylmethyl)-12-oxa-2,5,8-triazatridecanoate

There total 9 articles about tricyclo<3.3.1.1^3,7>dec-2-yl *,S^*)>-3-(1H-indol-3-ylmethyl)-3-methyl-4,9,11-trioxo-6-(phenylmethyl)-12-oxa-2,5,8-triazatridecanoate 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: 45.0%

3-chloro-3-oxopropanoic acid methyl ester (37517-81-0) + 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-4,9,11-trioxo-6-(phenylmethyl)-12-oxa-2,5,8-triazatridecanoate (130406-55-2)

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-4,9,11-trioxo-6-(phenylmethyl)-12-oxa-2,5,8-triazatridecanoate (130406-55-2)

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: 45 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-4,9,11-trioxo-6-(phenylmethyl)-12-oxa-2,5,8-triazatridecanoate (130406-55-2)

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: 45 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:

3-chloro-3-oxopropanoic acid methyl ester

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^*)>-3-<<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>-3-oxopropanoic acid

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