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

Base Information

• Chemical Name: N-((S)-3-[2-ethyl-4-(N-hydroxycarbamimidoyl)-6-methyl-phenoxy]-2-hydroxy-propyl)-2-hydroxy-acetamide
• CAS No.: 1150644-70-4
• Molecular Formula: C₁₅H₂₃N₃O₅
• Molecular Weight: 325.365

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

Chemical Property of N-((S)-3-[2-ethyl-4-(N-hydroxycarbamimidoyl)-6-methyl-phenoxy]-2-hydroxy-propyl)-2-hydroxy-acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of N-((S)-3-[2-ethyl-4-(N-hydroxycarbamimidoyl)-6-methyl-phenoxy]-2-hydroxy-propyl)-2-hydroxy-acetamide

There total 8 articles about N-((S)-3-[2-ethyl-4-(N-hydroxycarbamimidoyl)-6-methyl-phenoxy]-2-hydroxy-propyl)-2-hydroxy-acetamide 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: 87.0%

(S)-N-[3-(4-cyano-2-ethyl-6-methyl-phenoxy)-2-hydroxypropyl]-2-hydroxy-acetamide (1150644-71-5) → N-((S)-3-[2-ethyl-4-(N-hydroxycarbamimidoyl)-6-methyl-phenoxy]-2-hydroxy-propyl)-2-hydroxy-acetamide (1150644-70-4)

Guidance literature:

With hydroxylamine hydrochloride; sodium hydrogencarbonate; In methanol; at 65 ℃; for 18h; Reagent/catalyst; Solvent; Inert atmosphere;

DOI:10.1021/jm4014696

Reference yield:

6-ethyl-o-toluidine (24549-06-2) → N-((S)-3-[2-ethyl-4-(N-hydroxycarbamimidoyl)-6-methyl-phenoxy]-2-hydroxy-propyl)-2-hydroxy-acetamide (1150644-70-4)

Guidance literature:

Multi-step reaction with 7 steps

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

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

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

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

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

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

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

With 1-methyl-pyrrolidin-2-one; hexamethylenetetramine; sulfuric acid; hydroxylamine hydrochloride; ammonia; sodium hydrogencarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; sodium nitrite; diethylazodicarboxylate; In tetrahydrofuran; methanol; water; toluene; 2: |Duff Aldehyde Synthesis / 4: |Mitsunobu Displacement;

DOI:10.1021/jm4014696

Reference yield:

3-ethyl-4-hydroxy-5-methylbenzaldehyde (42900-98-1) → N-((S)-3-[2-ethyl-4-(N-hydroxycarbamimidoyl)-6-methyl-phenoxy]-2-hydroxy-propyl)-2-hydroxy-acetamide (1150644-70-4)

Guidance literature:

Multi-step reaction with 5 steps

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

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

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

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

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

With 1-methyl-pyrrolidin-2-one; hydroxylamine hydrochloride; ammonia; sodium hydrogencarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; toluene; 2: |Mitsunobu Displacement;

DOI:10.1021/jm4014696

upstream raw materials:

3-ethyl-4-hydroxy-5-methylbenzaldehyde

6-ethyl-o-toluidine

2-ethyl-6-methylphenol

3-ethyl-4-hydroxy-5-methyl-benzonitrile

Downstream raw materials:

N-((S)-3-{2-ethyl-4-[5-(2-ethylamino-6-methyl-pyrimidin-4-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamide

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

(S)-N-(3-(2-ethyl-4-(5-(6-isopropyl-5-methylpyridin-3-yl)-1,2,4-oxadiazol-3-yl)-6-methylphenoxy)-2-hydroxypropyl)-2-hydroxyacetamide

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

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