N¹-((R)-1-(4-fluorophenyl)ethyl)-N³-((2S,3S)-3-hydroxy-4-(4-((R)-1-hydroxy ethyl)-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-(4-((R)-1-hydroxy ethyl)-1H-1,2,3-triazol-1-yl)-1-phenylbutan-2-yl)-5-(N-methylmethylsulfonamido)isophthalamide
• CAS No.: 1385765-55-8
• Molecular Formula: C₃₂H₃₇FN₆O₆S
• Molecular Weight: 652.747

Synonyms:N¹-((R)-1-(4-fluorophenyl)ethyl)-N³-((2S,3S)-3-hydroxy-4-(4-((R)-1-hydroxy ethyl)-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-(4-((R)-1-hydroxy ethyl)-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-(4-((R)-1-hydroxy ethyl)-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-(4-((R)-1-hydroxy ethyl)-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: 62.7%

N1-((2S,3S)-4-azido-3-hydroxy-1-phenylbutan-2-yl)-N3-((R)-1-(4-fluorophenyl)ethyl)-5-(N-methylmethylsulfonamido)isophthalamide (1385766-25-5) + (R)-(+)-3-butyn-2-ol (42969-65-3) → N1-((R)-1-(4-fluorophenyl)ethyl)-N3-((2S,3S)-3-hydroxy-4-(4-((R)-1-hydroxy ethyl)-1H-1,2,3-triazol-1-yl)-1-phenylbutan-2-yl)-5-(N-methylmethylsulfonamido)isophthalamide (1385765-55-8)

Guidance literature:

With copper(l) iodide; sodium L-ascorbate; In tetrahydrofuran; water; at 50 ℃; for 12h;

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-(4-((R)-1-hydroxy ethyl)-1H-1,2,3-triazol-1-yl)-1-phenylbutan-2-yl)-5-(N-methylmethylsulfonamido)isophthalamide (1385765-55-8)

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: sodium L-ascorbate; copper(l) iodide / tetrahydrofuran; water / 12 h / 50 °C

With copper(l) iodide; benzotriazol-1-ol; sodium L-ascorbate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; 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-(4-((R)-1-hydroxy ethyl)-1H-1,2,3-triazol-1-yl)-1-phenylbutan-2-yl)-5-(N-methylmethylsulfonamido)isophthalamide (1385765-55-8)

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: sodium L-ascorbate; copper(l) iodide / tetrahydrofuran; water / 12 h / 50 °C

With copper(l) iodide; sodium azide; ammonium chloride; benzotriazol-1-ol; sodium L-ascorbate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.ejmech.2013.06.027

upstream raw materials:

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

(R)-(+)-3-butyn-2-ol

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

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

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