N¹-((R)-1-(4-Fluorophenyl)ethyl)-N³-((2S,3S)-3-hydroxy-4-(5-(hydroxymethyl)-1H-1,2,3-triazol-1-yl)-1-phenylbutan-2-yl)-5-(N-methylmethylsulfonamido)isophthalamide

Base Information

• Chemical Name: N¹-((R)-1-(4-Fluorophenyl)ethyl)-N³-((2S,3S)-3-hydroxy-4-(5-(hydroxymethyl)-1H-1,2,3-triazol-1-yl)-1-phenylbutan-2-yl)-5-(N-methylmethylsulfonamido)isophthalamide
• CAS No.: 1385764-67-9
• Molecular Formula: C₃₁H₃₅FN₆O₆S
• Molecular Weight: 638.72

Synonyms:N¹-((R)-1-(4-Fluorophenyl)ethyl)-N³-((2S,3S)-3-hydroxy-4-(5-(hydroxymethyl)-1H-1,2,3-triazol-1-yl)-1-phenylbutan-2-yl)-5-(N-methylmethylsulfonamido)isophthalamide

Chemical Property of N¹-((R)-1-(4-Fluorophenyl)ethyl)-N³-((2S,3S)-3-hydroxy-4-(5-(hydroxymethyl)-1H-1,2,3-triazol-1-yl)-1-phenylbutan-2-yl)-5-(N-methylmethylsulfonamido)isophthalamide

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Technology Process of N¹-((R)-1-(4-Fluorophenyl)ethyl)-N³-((2S,3S)-3-hydroxy-4-(5-(hydroxymethyl)-1H-1,2,3-triazol-1-yl)-1-phenylbutan-2-yl)-5-(N-methylmethylsulfonamido)isophthalamide

There total 4 articles about N¹-((R)-1-(4-Fluorophenyl)ethyl)-N³-((2S,3S)-3-hydroxy-4-(5-(hydroxymethyl)-1H-1,2,3-triazol-1-yl)-1-phenylbutan-2-yl)-5-(N-methylmethylsulfonamido)isophthalamide 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: 51.1%

N1-((2S,3S)-4-azido-3-hydroxy-1-phenylbutan-2-yl)-N3-((R)-1-(4-fluorophenyl)ethyl)-5-(N-methylmethylsulfonamido)isophthalamide (1385766-25-5) + propargyl alcohol (107-19-7) → N1-((R)-1-(4-Fluorophenyl)ethyl)-N3-((2S,3S)-3-hydroxy-4-(5-(hydroxymethyl)-1H-1,2,3-triazol-1-yl)-1-phenylbutan-2-yl)-5-(N-methylmethylsulfonamido)isophthalamide (1385764-67-9)

Guidance literature:

With tris(triphenylphosphine)ruthenium(II) chloride; In tetrahydrofuran; for 8h; Inert atmosphere; Reflux;

DOI:10.1016/j.ejmech.2013.06.027

Reference yield:

tert-butyl (2S,3S)-4-azido-3-hydroxy-1-phenylbutan-2-ylcarbamate (1385766-21-1) → N1-((R)-1-(4-Fluorophenyl)ethyl)-N3-((2S,3S)-3-hydroxy-4-(5-(hydroxymethyl)-1H-1,2,3-triazol-1-yl)-1-phenylbutan-2-yl)-5-(N-methylmethylsulfonamido)isophthalamide (1385764-67-9)

Guidance literature:

Multi-step reaction with 3 steps

1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C

2: benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 20 °C

3: tris(triphenylphosphine)ruthenium(II) chloride / tetrahydrofuran / 8 h / Inert atmosphere; Reflux

With tris(triphenylphosphine)ruthenium(II) chloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.ejmech.2013.06.027

Reference yield:

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane (98760-08-8) → N1-((R)-1-(4-Fluorophenyl)ethyl)-N3-((2S,3S)-3-hydroxy-4-(5-(hydroxymethyl)-1H-1,2,3-triazol-1-yl)-1-phenylbutan-2-yl)-5-(N-methylmethylsulfonamido)isophthalamide (1385764-67-9)

Guidance literature:

Multi-step reaction with 4 steps

1: ammonium chloride; sodium azide / methanol / Reflux

2: trifluoroacetic acid / dichloromethane / 3 h / 20 °C

3: benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 20 °C

4: tris(triphenylphosphine)ruthenium(II) chloride / tetrahydrofuran / 8 h / Inert atmosphere; Reflux

With tris(triphenylphosphine)ruthenium(II) chloride; sodium azide; ammonium chloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.ejmech.2013.06.027

upstream raw materials:

tert-butyl (2S,3S)-4-azido-3-hydroxy-1-phenylbutan-2-ylcarbamate

N¹-((2S,3S)-4-azido-3-hydroxy-1-phenylbutan-2-yl)-N³-((R)-1-(4-fluorophenyl)ethyl)-5-(N-methylmethylsulfonamido)isophthalamide

propargyl alcohol

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

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