4-(3-(4-benzyloxyphenyl)-propenoyl-amino)-1-(tert-butyloxycarbonyl)piperidine-4-carboxylic acid tryptamide

Base Information

Chemical Name:4-(3-(4-benzyloxyphenyl)-propenoyl-amino)-1-(tert-butyloxycarbonyl)piperidine-4-carboxylic acid tryptamide
CAS No.:940290-04-0
Molecular Formula:C₃₇H₄₂N₄O₅
Molecular Weight:622.764
Hs Code.:

Synonyms:4-(3-(4-benzyloxyphenyl)-propenoyl-amino)-1-(tert-butyloxycarbonyl)piperidine-4-carboxylic acid tryptamide

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Chemical Property of 4-(3-(4-benzyloxyphenyl)-propenoyl-amino)-1-(tert-butyloxycarbonyl)piperidine-4-carboxylic acid tryptamide

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Technology Process of 4-(3-(4-benzyloxyphenyl)-propenoyl-amino)-1-(tert-butyloxycarbonyl)piperidine-4-carboxylic acid tryptamide

There total 10 articles about 4-(3-(4-benzyloxyphenyl)-propenoyl-amino)-1-(tert-butyloxycarbonyl)piperidine-4-carboxylic acid tryptamide 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: 41.0%

: 940290-03-9
4-amino-1-(tert-butyloxycarbonyl)piperidine-4-carboxylic acid tryptamide

: 6272-45-3,227105-11-5
(E)-4-benzyloxycinnamic acid

: 940290-04-0
4-(3-(4-benzyloxyphenyl)-propenoyl-amino)-1-(tert-butyloxycarbonyl)piperidine-4-carboxylic acid tryptamide

Guidance literature:: (E)-4-benzyloxycinnamic acid; With chloroformic acid ethyl ester; triethylamine; In tetrahydrofuran; at -20 ℃; for 1h;

4-amino-1-(tert-butyloxycarbonyl)piperidine-4-carboxylic acid tryptamide; With triethylamine; In tetrahydrofuran; at 20 ℃; for 72h; Further stages.;
DOI:10.1016/j.bmcl.2007.02.023

Reference yield:

: 940290-02-8
4-[(benzyloxycarbonyl)amino]-1-(tert-butyloxycarbonyl)piperidine-4-carboxylic acid tryptamide

: 940290-04-0
4-(3-(4-benzyloxyphenyl)-propenoyl-amino)-1-(tert-butyloxycarbonyl)piperidine-4-carboxylic acid tryptamide

Guidance literature:: Multi-step reaction with 2 steps

1.1: 89 percent / ammonium formate / Pd/C / methanol / 3 h / 20 °C

2.1: Et₃N; ethyl chloroformate / tetrahydrofuran / 1 h / -20 °C

2.2: 41 percent / Et₃N / tetrahydrofuran / 72 h / 20 °C

With ammonium formate; chloroformic acid ethyl ester; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol;
DOI:10.1016/j.bmcl.2007.02.023

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 940290-04-0
4-(3-(4-benzyloxyphenyl)-propenoyl-amino)-1-(tert-butyloxycarbonyl)piperidine-4-carboxylic acid tryptamide

Guidance literature:: Multi-step reaction with 6 steps

1.1: 86 percent / Et₃N; DMAP / 1,2-dimethoxy-ethane / 20 °C

2.1: 76 percent / aq. NaOH / 1,2-dimethoxy-ethane / 48 h / 20 °C

3.1: 78 percent / K₂CO₃ / H₂O; dioxane / 20 °C

4.1: Et₃N; ethyl chloroformate / CH₂Cl₂ / 1 h / -20 °C

4.2: 67 percent / Et₃N / CH₂Cl₂ / 20 °C

5.1: 89 percent / ammonium formate / Pd/C / methanol / 3 h / 20 °C

6.1: Et₃N; ethyl chloroformate / tetrahydrofuran / 1 h / -20 °C

6.2: 41 percent / Et₃N / tetrahydrofuran / 72 h / 20 °C

With dmap; sodium hydroxide; ammonium formate; chloroformic acid ethyl ester; potassium carbonate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; 1,2-dimethoxyethane; dichloromethane; water;
DOI:10.1016/j.bmcl.2007.02.023