propylcarbamic acid 3-(2-[benzyloxycarbonyl-[4-(4-benzyloxyphenyl)butyl]amino]-ethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl ester

Base Information

• Chemical Name: propylcarbamic acid 3-(2-[benzyloxycarbonyl-[4-(4-benzyloxyphenyl)butyl]amino]-ethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl ester
• CAS No.: 192773-97-0
• Molecular Formula: C₄₇H₅₁N₃O₅
• Molecular Weight: 737.939

Synonyms:propylcarbamic acid 3-(2-[benzyloxycarbonyl-[4-(4-benzyloxyphenyl)butyl]amino]-ethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl ester

Chemical Property of propylcarbamic acid 3-(2-[benzyloxycarbonyl-[4-(4-benzyloxyphenyl)butyl]amino]-ethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl ester

Chemical Property:

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Technology Process of propylcarbamic acid 3-(2-[benzyloxycarbonyl-[4-(4-benzyloxyphenyl)butyl]amino]-ethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl ester

There total 15 articles about propylcarbamic acid 3-(2-[benzyloxycarbonyl-[4-(4-benzyloxyphenyl)butyl]amino]-ethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl 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:

5-benzyloxytryptamine (20776-45-8) → propylcarbamic acid 3-(2-[benzyloxycarbonyl-[4-(4-benzyloxyphenyl)butyl]amino]-ethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl ester (192773-97-0)

Guidance literature:

Multi-step reaction with 12 steps

1.1: tetrahydrofuran / Heating

2.1: pyridine hydrobromide perbromide / tetrahydrofuran; CHCl₃

3.1: Na₂CO₃; LiCl; Pd(PPh₃)4 / toluene; ethanol / 1.25 h / Heating

4.1: aq. hydrazine / tetrahydrofuran; ethanol

5.1: HOBT; EDAC / dimethylformamide; CH₂Cl₂

6.1: BH₃*THF / tetrahydrofuran / 3 h / Heating

6.2: N,N-dimethylethanolamine / methanol; tetrahydrofuran / 3 h / Heating

7.1: H₂ / 10 percent Pd/C / ethyl acetate / 48 h / 760 Torr

8.1: aq. hydrazine / tetrahydrofuran; ethanol

9.1: 91 percent / HOBT; EDAC / CH₂Cl₂

10.1: BH₃*THF / tetrahydrofuran / Heating

10.2: N,N-dimethylethanolamine / methanol; tetrahydrofuran / Heating

11.1: Huenig's base / CH₂Cl₂ / -78 °C

12.1: pyridine / CH₂Cl₂ / 0.5 h / 0 °C

With pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; borane-THF; hydrogen; pyridinium hydrobromide perbromide; sodium carbonate; benzotriazol-1-ol; hydrazine hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; chloroform; ethyl acetate; N,N-dimethyl-formamide; toluene; 3.1: modified Suzuki reaction;

DOI:10.1016/S0960-894X(00)00708-3

Reference yield:

N-[2-(5-benzyloxy-indol-3-yl)-ethyl]-phthalimide (53157-45-2) → propylcarbamic acid 3-(2-[benzyloxycarbonyl-[4-(4-benzyloxyphenyl)butyl]amino]-ethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl ester (192773-97-0)

Guidance literature:

Multi-step reaction with 11 steps

1.1: pyridine hydrobromide perbromide / tetrahydrofuran; CHCl₃

2.1: Na₂CO₃; LiCl; Pd(PPh₃)4 / toluene; ethanol / 1.25 h / Heating

3.1: aq. hydrazine / tetrahydrofuran; ethanol

4.1: HOBT; EDAC / dimethylformamide; CH₂Cl₂

5.1: BH₃*THF / tetrahydrofuran / 3 h / Heating

5.2: N,N-dimethylethanolamine / methanol; tetrahydrofuran / 3 h / Heating

6.1: H₂ / 10 percent Pd/C / ethyl acetate / 48 h / 760 Torr

7.1: aq. hydrazine / tetrahydrofuran; ethanol

8.1: 91 percent / HOBT; EDAC / CH₂Cl₂

9.1: BH₃*THF / tetrahydrofuran / Heating

9.2: N,N-dimethylethanolamine / methanol; tetrahydrofuran / Heating

10.1: Huenig's base / CH₂Cl₂ / -78 °C

11.1: pyridine / CH₂Cl₂ / 0.5 h / 0 °C

With pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; borane-THF; hydrogen; pyridinium hydrobromide perbromide; sodium carbonate; benzotriazol-1-ol; hydrazine hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; chloroform; ethyl acetate; N,N-dimethyl-formamide; toluene; 2.1: modified Suzuki reaction;

DOI:10.1016/S0960-894X(00)00708-3

Reference yield:

2-[2-(5-benzyloxy-2-bromo-1H-indol-3-yl)ethyl]isoindole-1,3-dione (192182-48-2) → propylcarbamic acid 3-(2-[benzyloxycarbonyl-[4-(4-benzyloxyphenyl)butyl]amino]-ethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl ester (192773-97-0)

Guidance literature:

Multi-step reaction with 10 steps

1.1: Na₂CO₃; LiCl; Pd(PPh₃)4 / toluene; ethanol / 1.25 h / Heating

2.1: aq. hydrazine / tetrahydrofuran; ethanol

3.1: HOBT; EDAC / dimethylformamide; CH₂Cl₂

4.1: BH₃*THF / tetrahydrofuran / 3 h / Heating

4.2: N,N-dimethylethanolamine / methanol; tetrahydrofuran / 3 h / Heating

5.1: H₂ / 10 percent Pd/C / ethyl acetate / 48 h / 760 Torr

6.1: aq. hydrazine / tetrahydrofuran; ethanol

7.1: 91 percent / HOBT; EDAC / CH₂Cl₂

8.1: BH₃*THF / tetrahydrofuran / Heating

8.2: N,N-dimethylethanolamine / methanol; tetrahydrofuran / Heating

9.1: Huenig's base / CH₂Cl₂ / -78 °C

10.1: pyridine / CH₂Cl₂ / 0.5 h / 0 °C

With pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; borane-THF; hydrogen; sodium carbonate; benzotriazol-1-ol; hydrazine hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; 1.1: modified Suzuki reaction;

DOI:10.1016/S0960-894X(00)00708-3

upstream raw materials:

propylamine

bis(trichloromethyl) carbonate

[4-(4-benzyloxyphenyl)-butyl]-[2-[2-(3,5-dimethylphenyl)-5-hydroxy-1H-indol-3-yl]ethyl]carbamic acid benzyl ester

4-(4-hydroxyphenyl)butanoic acid

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