N-((S)-3-{4-[5-(6-cyclopentyl-5-methylpyridin-3-yl)[1,2,4]-oxadiazol-3-yl]-2-ethyl-6-methylphenoxy}-2-hydroxypropyl)-2-hydroxyacetamide

Base Information

Chemical Name:N-((S)-3-{4-[5-(6-cyclopentyl-5-methylpyridin-3-yl)[1,2,4]-oxadiazol-3-yl]-2-ethyl-6-methylphenoxy}-2-hydroxypropyl)-2-hydroxyacetamide
CAS No.:1516901-66-8
Molecular Formula:C₂₇H₃₄N₄O₅
Molecular Weight:494.591
Hs Code.:

Synonyms:N-((S)-3-{4-[5-(6-cyclopentyl-5-methylpyridin-3-yl)[1,2,4]-oxadiazol-3-yl]-2-ethyl-6-methylphenoxy}-2-hydroxypropyl)-2-hydroxyacetamide

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Chemical Property of N-((S)-3-{4-[5-(6-cyclopentyl-5-methylpyridin-3-yl)[1,2,4]-oxadiazol-3-yl]-2-ethyl-6-methylphenoxy}-2-hydroxypropyl)-2-hydroxyacetamide

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Technology Process of N-((S)-3-{4-[5-(6-cyclopentyl-5-methylpyridin-3-yl)[1,2,4]-oxadiazol-3-yl]-2-ethyl-6-methylphenoxy}-2-hydroxypropyl)-2-hydroxyacetamide

There total 12 articles about N-((S)-3-{4-[5-(6-cyclopentyl-5-methylpyridin-3-yl)[1,2,4]-oxadiazol-3-yl]-2-ethyl-6-methylphenoxy}-2-hydroxypropyl)-2-hydroxyacetamide 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: 73.0%

: 1122093-38-2
6-cyclopentyl-5-methylnicotinic acid

: 1150644-70-4
N-((S)-3-[2-ethyl-4-(N-hydroxycarbamimidoyl)-6-methyl-phenoxy]-2-hydroxy-propyl)-2-hydroxy-acetamide

: 1516901-66-8
N-((S)-3-{4-[5-(6-cyclopentyl-5-methylpyridin-3-yl)[1,2,4]-oxadiazol-3-yl]-2-ethyl-6-methylphenoxy}-2-hydroxypropyl)-2-hydroxyacetamide

Guidance literature:: 6-cyclopentyl-5-methylnicotinic acid; N-((S)-3-[2-ethyl-4-(N-hydroxycarbamimidoyl)-6-methyl-phenoxy]-2-hydroxy-propyl)-2-hydroxy-acetamide; With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; Inert atmosphere;

In 1,4-dioxane; at 100 ℃; Reagent/catalyst; Inert atmosphere;
DOI:10.1021/jm4014696

Reference yield:

: 42900-98-1
3-ethyl-4-hydroxy-5-methylbenzaldehyde

: 1516901-66-8
N-((S)-3-{4-[5-(6-cyclopentyl-5-methylpyridin-3-yl)[1,2,4]-oxadiazol-3-yl]-2-ethyl-6-methylphenoxy}-2-hydroxypropyl)-2-hydroxyacetamide

Guidance literature:: Multi-step reaction with 6 steps

1.1: 1-methyl-pyrrolidin-2-one; hydroxylamine hydrochloride / 3 h / 80 - 100 °C / Microwave irradiation; Inert atmosphere

2.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 18 h / 0 - 20 °C / Inert atmosphere

3.1: ammonia / methanol / 18 h / 65 °C / Inert atmosphere; Sealed tube

4.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / 18 h / 20 °C / Inert atmosphere

5.1: hydroxylamine hydrochloride; sodium hydrogencarbonate / methanol / 18 h / 65 °C / Inert atmosphere

6.1: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

6.2: 100 °C / Inert atmosphere

With 1-methyl-pyrrolidin-2-one; hydroxylamine hydrochloride; ammonia; sodium hydrogencarbonate; benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; toluene; 2.1: |Mitsunobu Displacement;
DOI:10.1021/jm4014696

Reference yield:

: 24549-06-2
6-ethyl-o-toluidine

: 1516901-66-8
N-((S)-3-{4-[5-(6-cyclopentyl-5-methylpyridin-3-yl)[1,2,4]-oxadiazol-3-yl]-2-ethyl-6-methylphenoxy}-2-hydroxypropyl)-2-hydroxyacetamide

Guidance literature:: Multi-step reaction with 8 steps

1.1: sulfuric acid; sodium nitrite / water / 19 h / 0 °C / Cooling with ice

2.1: hexamethylenetetramine / water / 120 °C / Reflux; Dean-Stark

3.1: 1-methyl-pyrrolidin-2-one; hydroxylamine hydrochloride / 3 h / 80 - 100 °C / Microwave irradiation; Inert atmosphere

4.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 18 h / 0 - 20 °C / Inert atmosphere

5.1: ammonia / methanol / 18 h / 65 °C / Inert atmosphere; Sealed tube

6.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / 18 h / 20 °C / Inert atmosphere

7.1: hydroxylamine hydrochloride; sodium hydrogencarbonate / methanol / 18 h / 65 °C / Inert atmosphere

8.1: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

8.2: 100 °C / Inert atmosphere

With 1-methyl-pyrrolidin-2-one; hexamethylenetetramine; sulfuric acid; hydroxylamine hydrochloride; ammonia; sodium hydrogencarbonate; benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium nitrite; diethylazodicarboxylate; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; toluene; 2.1: |Duff Aldehyde Synthesis / 4.1: |Mitsunobu Displacement;
DOI:10.1021/jm4014696