(3S,6S)-1-(o-azidobenzoyl)-4-(2'',4''-dimethoxybenzyl)-3-(3'-indolylmethyl)-6-methyl-2,5-piperazinedione

Base Information

Chemical Name:(3S,6S)-1-(o-azidobenzoyl)-4-(2'',4''-dimethoxybenzyl)-3-(3'-indolylmethyl)-6-methyl-2,5-piperazinedione
CAS No.:300766-79-4
Molecular Formula:C₃₀H₂₈N₆O₅
Molecular Weight:552.59
Hs Code.:

Synonyms:(3S,6S)-1-(o-azidobenzoyl)-4-(2'',4''-dimethoxybenzyl)-3-(3'-indolylmethyl)-6-methyl-2,5-piperazinedione

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Chemical Property of (3S,6S)-1-(o-azidobenzoyl)-4-(2'',4''-dimethoxybenzyl)-3-(3'-indolylmethyl)-6-methyl-2,5-piperazinedione

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Technology Process of (3S,6S)-1-(o-azidobenzoyl)-4-(2'',4''-dimethoxybenzyl)-3-(3'-indolylmethyl)-6-methyl-2,5-piperazinedione

There total 5 articles about (3S,6S)-1-(o-azidobenzoyl)-4-(2'',4''-dimethoxybenzyl)-3-(3'-indolylmethyl)-6-methyl-2,5-piperazinedione 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: 27.0%

: 34897-85-3
o-azidobenzoyl chloride

: 300766-86-3
(3S,6S)-6-(3'-indolylmethyl)-3-methyl-1-(2,4-dimethoxybenzyl)-2,5-piperazinedione

: 300766-79-4
(3S,6S)-1-(o-azidobenzoyl)-4-(2'',4''-dimethoxybenzyl)-3-(3'-indolylmethyl)-6-methyl-2,5-piperazinedione

: (3S,6S)-1-(o-azidobenzoyl)-4-(2'',4''-dimethoxybenzyl)-3-[1'-(o-azidobenzoyl)-3'-indolylmethyl]-6-methyl-2,5-piperazinedione

Guidance literature:: (3S,6S)-6-(3'-indolylmethyl)-3-methyl-1-(2,4-dimethoxybenzyl)-2,5-piperazinedione; With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 ℃; for 0.25h;

o-azidobenzoyl chloride; In tetrahydrofuran; toluene; at -78 - 20 ℃; for 19h;
DOI:10.3987/com-00-8942

Reference yield:

: methyl (S)-N'-(2'',4''-dimethoxybenzyliden)tryptophanate

: 300766-79-4
(3S,6S)-1-(o-azidobenzoyl)-4-(2'',4''-dimethoxybenzyl)-3-(3'-indolylmethyl)-6-methyl-2,5-piperazinedione

Guidance literature:: Multi-step reaction with 3 steps

1.1: 87 percent / NaBH₄ / methanol / 15 h / 20 °C

2.1: DCC / tetrahydrofuran / 44 h / 20 °C

2.2: 759 mg / 5 h / 200 °C

3.1: potassium hexamethyldisilazide / tetrahydrofuran; toluene / 0.25 h / -78 °C

3.2: 27 percent / tetrahydrofuran; toluene / 19 h / -78 - 20 °C

With sodium tetrahydroborate; potassium hexamethylsilazane; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; toluene; 1.1: Reduction / 2.1: Acylation / 2.2: Cyclization / 3.1: deprotonation / 3.2: Acylation;
DOI:10.3987/com-00-8942

Reference yield:

: 168766-64-1
methyl (S)-N'-(2,4-dimethoxybenzyl)tryptophanate

: 300766-79-4
(3S,6S)-1-(o-azidobenzoyl)-4-(2'',4''-dimethoxybenzyl)-3-(3'-indolylmethyl)-6-methyl-2,5-piperazinedione

Guidance literature:: Multi-step reaction with 2 steps

1.1: DCC / tetrahydrofuran / 44 h / 20 °C

1.2: 759 mg / 5 h / 200 °C

2.1: potassium hexamethyldisilazide / tetrahydrofuran; toluene / 0.25 h / -78 °C

2.2: 27 percent / tetrahydrofuran; toluene / 19 h / -78 - 20 °C

With potassium hexamethylsilazane; dicyclohexyl-carbodiimide; In tetrahydrofuran; toluene; 1.1: Acylation / 1.2: Cyclization / 2.1: deprotonation / 2.2: Acylation;
DOI:10.3987/com-00-8942