tricyclo<3.3.1.1^3,7>dec-2-yl (+/-)-<2-(1H-indol-3-yl)-1-<<<(4-nitrophenyl)methoxy>carbonyl>amino>ethyl>carbamate

Base Information

• Chemical Name: tricyclo<3.3.1.1^3,7>dec-2-yl (+/-)-<2-(1H-indol-3-yl)-1-<<<(4-nitrophenyl)methoxy>carbonyl>amino>ethyl>carbamate
• CAS No.: 142620-70-0
• Molecular Formula: C₂₉H₃₂N₄O₆
• Molecular Weight: 532.596

Synonyms:tricyclo<3.3.1.1^3,7>dec-2-yl (+/-)-<2-(1H-indol-3-yl)-1-<<<(4-nitrophenyl)methoxy>carbonyl>amino>ethyl>carbamate

Chemical Property of tricyclo<3.3.1.1^3,7>dec-2-yl (+/-)-<2-(1H-indol-3-yl)-1-<<<(4-nitrophenyl)methoxy>carbonyl>amino>ethyl>carbamate

Chemical Property:

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Technology Process of tricyclo<3.3.1.1^3,7>dec-2-yl (+/-)-<2-(1H-indol-3-yl)-1-<<<(4-nitrophenyl)methoxy>carbonyl>amino>ethyl>carbamate

There total 5 articles about tricyclo<3.3.1.1^3,7>dec-2-yl (+/-)-<2-(1H-indol-3-yl)-1-<<<(4-nitrophenyl)methoxy>carbonyl>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:

4-nitrobenzyl chloride (619-73-8) + [2-(1H-Indol-3-yl)-1-isocyanato-ethyl]-carbamic acid adamantan-2-yl ester (187610-05-5) → tricyclo<3.3.1.13,7>dec-2-yl (+/-)-<2-(1H-indol-3-yl)-1-<<<(4-nitrophenyl)methoxy>carbonyl>amino>ethyl>carbamate (142620-70-0)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; In toluene; at 40 ℃; for 15h; Yield given;

DOI:10.1021/jm00086a017

Reference yield:

2-adamantyl chloroformate (53120-53-9) → tricyclo<3.3.1.13,7>dec-2-yl (+/-)-<2-(1H-indol-3-yl)-1-<<<(4-nitrophenyl)methoxy>carbonyl>amino>ethyl>carbamate (142620-70-0)

Guidance literature:

Multi-step reaction with 4 steps

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

2: 1.) N-methylmorpholine, isobutyl chloroformate, 2.) trimethylsilyl azide / 1.) THF, -10 deg C, 20 min, 2.) THF, -10 deg C, 1 h

3: toluene / 0.5 h / 40 °C

4: 1,4-diazabicyclo<2.2.2>octane (DABCO) / toluene / 15 h / 40 °C

With 4-methyl-morpholine; 1,4-diaza-bicyclo[2.2.2]octane; sodium hydroxide; trimethylsilylazide; sodium hydrogencarbonate; isobutyl chloroformate; In 1,4-dioxane; toluene;

DOI:10.1021/jm00086a017

Reference yield:

tricyclo<3.3.1.13,7>dec-2-yl <1-carboxy-2-(1H-indol-3-yl)ethyl>carbamate (139657-07-1) → tricyclo<3.3.1.13,7>dec-2-yl (+/-)-<2-(1H-indol-3-yl)-1-<<<(4-nitrophenyl)methoxy>carbonyl>amino>ethyl>carbamate (142620-70-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) N-methylmorpholine, isobutyl chloroformate, 2.) trimethylsilyl azide / 1.) THF, -10 deg C, 20 min, 2.) THF, -10 deg C, 1 h

2: toluene / 0.5 h / 40 °C

3: 1,4-diazabicyclo<2.2.2>octane (DABCO) / toluene / 15 h / 40 °C

With 4-methyl-morpholine; 1,4-diaza-bicyclo[2.2.2]octane; trimethylsilylazide; isobutyl chloroformate; In toluene;

DOI:10.1021/jm00086a017

upstream raw materials:

4-nitrobenzyl chloride

[2-(1H-Indol-3-yl)-1-isocyanato-ethyl]-carbamic acid adamantan-2-yl ester

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:

Acetic acid 2-[1-(adamantan-2-yloxycarbonylamino)-2-(1H-indol-3-yl)-ethylcarbamoyl]-3-phenyl-propyl ester

tricyclo<3.3.1.1^3,7>dec-2-yl (+/-)-<1-<<2-(hydroxymethyl)-1-oxo-3-phenylpropyl>amino>-2-(1H-indol-3-yl)ethyl>carbamate

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