methyl 5-{[(E)-5-benzyloxy-4-ethylpent-4-enoyl]-[2-(1-methyl-1H-indol-3-yl)ethyl]amino}-1,3,4-oxadiazole-2-carboxylate

Base Information

Chemical Name:methyl 5-{[(E)-5-benzyloxy-4-ethylpent-4-enoyl]-[2-(1-methyl-1H-indol-3-yl)ethyl]amino}-1,3,4-oxadiazole-2-carboxylate
CAS No.:473742-80-2
Molecular Formula:C₂₉H₃₂N₄O₅
Molecular Weight:516.597
Hs Code.:

Synonyms:methyl 5-{[(E)-5-benzyloxy-4-ethylpent-4-enoyl]-[2-(1-methyl-1H-indol-3-yl)ethyl]amino}-1,3,4-oxadiazole-2-carboxylate

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Chemical Property of methyl 5-{[(E)-5-benzyloxy-4-ethylpent-4-enoyl]-[2-(1-methyl-1H-indol-3-yl)ethyl]amino}-1,3,4-oxadiazole-2-carboxylate

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Technology Process of methyl 5-{[(E)-5-benzyloxy-4-ethylpent-4-enoyl]-[2-(1-methyl-1H-indol-3-yl)ethyl]amino}-1,3,4-oxadiazole-2-carboxylate

There total 9 articles about methyl 5-{[(E)-5-benzyloxy-4-ethylpent-4-enoyl]-[2-(1-methyl-1H-indol-3-yl)ethyl]amino}-1,3,4-oxadiazole-2-carboxylate 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: 96.0%

: 473742-38-0
methyl 5-[(2-(1-methyl-1H-indol-3-yl)ethyl)amino]-1,3,4-oxadiazole-2-carboxylate

: 473742-40-4
(E)-5-(benzyloxy)-4-ethylpent-4-enoic acid

: 473742-80-2
methyl 5-{[(E)-5-benzyloxy-4-ethylpent-4-enoyl]-[2-(1-methyl-1H-indol-3-yl)ethyl]amino}-1,3,4-oxadiazole-2-carboxylate

Guidance literature:: With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃; for 4h;
DOI:10.1002/anie.200503024

Reference yield:

: (benzyloxymethyl)triphenylphosphonium bromide

: 473742-80-2
methyl 5-{[(E)-5-benzyloxy-4-ethylpent-4-enoyl]-[2-(1-methyl-1H-indol-3-yl)ethyl]amino}-1,3,4-oxadiazole-2-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: NaHMDS / tetrahydrofuran / -78 - -40 °C

1.2: 11.0 g / tetrahydrofuran / -40 - 25 °C

2.1: aq. LiOH / tetrahydrofuran; methanol / 0 - 25 °C

3.1: 96 percent / EDCI; DMAP / CH₂Cl₂ / 4 h / 20 °C

With dmap; lithium hydroxide; sodium hexamethyldisilazane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1002/anie.200503024

Reference yield:

: 473742-36-8
N¹-methyl-N-(imidazol-1-ylcarbonyl)tryptamine

: 473742-80-2
methyl 5-{[(E)-5-benzyloxy-4-ethylpent-4-enoyl]-[2-(1-methyl-1H-indol-3-yl)ethyl]amino}-1,3,4-oxadiazole-2-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: 93 percent / AcOH / tetrahydrofuran / 16 h / 40 °C

2: 83 percent / Et₃N; TsCl / CH₂Cl₂ / 16 h / 23 °C

3: 96 percent / EDCI; DMAP / CH₂Cl₂ / 4 h / 20 °C

With dmap; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; p-toluenesulfonyl chloride; In tetrahydrofuran; dichloromethane;
DOI:10.1002/anie.200503024