(2S,4R)-5-biphenyl-4-yl-2-hydroxymethyl-2-methyl-4-[(3H-[1,2,3]triazole-4-carbonyl)amino]pentanoic acid (R)-1-cyclohexyloxycarbonyloxyethyl ester

Base Information

• Chemical Name: (2S,4R)-5-biphenyl-4-yl-2-hydroxymethyl-2-methyl-4-[(3H-[1,2,3]triazole-4-carbonyl)amino]pentanoic acid (R)-1-cyclohexyloxycarbonyloxyethyl ester
• CAS No.: 1394049-73-0
• Molecular Formula: C₃₁H₃₈N₄O₇
• Molecular Weight: 578.665
• Mol file: 1394049-73-0.mol

Synonyms:(2S,4R)-5-biphenyl-4-yl-2-hydroxymethyl-2-methyl-4-[(3H-[1,2,3]triazole-4-carbonyl)amino]pentanoic acid (R)-1-cyclohexyloxycarbonyloxyethyl ester

Chemical Property of (2S,4R)-5-biphenyl-4-yl-2-hydroxymethyl-2-methyl-4-[(3H-[1,2,3]triazole-4-carbonyl)amino]pentanoic acid (R)-1-cyclohexyloxycarbonyloxyethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4R)-5-biphenyl-4-yl-2-hydroxymethyl-2-methyl-4-[(3H-[1,2,3]triazole-4-carbonyl)amino]pentanoic acid (R)-1-cyclohexyloxycarbonyloxyethyl ester

There total 7 articles about (2S,4R)-5-biphenyl-4-yl-2-hydroxymethyl-2-methyl-4-[(3H-[1,2,3]triazole-4-carbonyl)amino]pentanoic acid (R)-1-cyclohexyloxycarbonyloxyethyl ester 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:

1H-1,2,3-triazole-4-carboxylic acid (16681-70-2) + (2S,4R)-4-amino-5-biphenyl-4-yl-2-hydroxymethyl-2-methyl-pentanoic acid 1-cyclohexyloxycarbonyloxy-ethyl ester (1394050-62-4) → (2S,4R)-5-Biphenyl-4-yl-2-hydroxymethyl-2-methyl-4-[(3H-[1,2,3]triazole-4-carbonyl)-amino]-pentanoic acid (S)-1-cyclohexyloxycarbonyloxy-ethyl ester (1394049-75-2) + (2S,4R)-5-biphenyl-4-yl-2-hydroxymethyl-2-methyl-4-[(3H-[1,2,3]triazole-4-carbonyl)amino]pentanoic acid (R)-1-cyclohexyloxycarbonyloxyethyl ester (1394049-73-0)

Guidance literature:

1H-1,2,3-triazole-4-carboxylic acid; With 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V); N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 0.0833333h; Inert atmosphere;

(2S,4R)-4-amino-5-biphenyl-4-yl-2-hydroxymethyl-2-methyl-pentanoic acid 1-cyclohexyloxycarbonyloxy-ethyl ester; In N,N-dimethyl-formamide; for 0.25h; Inert atmosphere;

Reference yield:

C33H45NO8 → (2S,4R)-5-Biphenyl-4-yl-2-hydroxymethyl-2-methyl-4-[(3H-[1,2,3]triazole-4-carbonyl)-amino]-pentanoic acid (S)-1-cyclohexyloxycarbonyloxy-ethyl ester (1394049-75-2) + (2S,4R)-5-biphenyl-4-yl-2-hydroxymethyl-2-methyl-4-[(3H-[1,2,3]triazole-4-carbonyl)amino]pentanoic acid (R)-1-cyclohexyloxycarbonyloxyethyl ester (1394049-73-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: hydrogenchloride / 1,4-dioxane; acetonitrile / 0.5 h / Inert atmosphere

2.1: N-ethyl-N,N-diisopropylamine; 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V) / N,N-dimethyl-formamide / 0.08 h / 20 °C / Inert atmosphere

2.2: 0.25 h / Inert atmosphere

With hydrogenchloride; 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V); N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; N,N-dimethyl-formamide; acetonitrile;

Reference yield:

(2R)-3-(biphenyl-4-yl)-2-[(tert-butoxycarbonyl)amino]propanoic acid (128779-47-5) → (2S,4R)-5-Biphenyl-4-yl-2-hydroxymethyl-2-methyl-4-[(3H-[1,2,3]triazole-4-carbonyl)-amino]-pentanoic acid (S)-1-cyclohexyloxycarbonyloxy-ethyl ester (1394049-75-2) + (2S,4R)-5-biphenyl-4-yl-2-hydroxymethyl-2-methyl-4-[(3H-[1,2,3]triazole-4-carbonyl)amino]pentanoic acid (R)-1-cyclohexyloxycarbonyloxyethyl ester (1394049-73-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 9 h / -5 °C / Inert atmosphere

2.1: acetic acid / dichloromethane / 0.5 h / -5 °C / Inert atmosphere

2.2: 2 h / -5 °C / Inert atmosphere

3.1: potassium carbonate / N,N-dimethyl-formamide / 0 - 23 °C / Inert atmosphere

4.1: samarium diiodide / water; tetrahydrofuran / 0.25 h / Inert atmosphere

5.1: triethylamine / acetone / 24 h / Inert atmosphere; Reflux

6.1: hydrogenchloride / 1,4-dioxane; acetonitrile / 0.5 h / Inert atmosphere

7.1: N-ethyl-N,N-diisopropylamine; 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V) / N,N-dimethyl-formamide / 0.08 h / 20 °C / Inert atmosphere

7.2: 0.25 h / Inert atmosphere

With hydrogenchloride; dmap; samarium diiodide; 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V); potassium carbonate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile;

upstream raw materials:

(2R)-3-(biphenyl-4-yl)-2-[(tert-butoxycarbonyl)amino]propanoic acid

1H-1,2,3-triazole-4-carboxylic acid

(2S,4R)-4-amino-5-biphenyl-4-yl-2-hydroxymethyl-2-methyl-pentanoic acid 1-cyclohexyloxycarbonyloxy-ethyl ester

[(R)-1-biphenyl-4-ylmethyl-2-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-yl)-2-oxoethyl]carbamic acid t-butyl ester

Refernces