(2S,4R)-5-biphenyl-4-yl-2-isobutyryloxymethyl-2-methyl-4-[(3H-[1,2,3]triazole-4-carbonyl)amino]pentanoic Acid

Base Information

• Chemical Name: (2S,4R)-5-biphenyl-4-yl-2-isobutyryloxymethyl-2-methyl-4-[(3H-[1,2,3]triazole-4-carbonyl)amino]pentanoic Acid
• CAS No.: 1562404-16-3
• Molecular Formula: C₂₆H₃₀N₄O₅
• Molecular Weight: 478.548
• Mol file: 1562404-16-3.mol

Synonyms:(2S,4R)-5-biphenyl-4-yl-2-isobutyryloxymethyl-2-methyl-4-[(3H-[1,2,3]triazole-4-carbonyl)amino]pentanoic Acid

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 14 articles about (2S,4R)-5-biphenyl-4-yl-2-isobutyryloxymethyl-2-methyl-4-[(3H-[1,2,3]triazole-4-carbonyl)amino]pentanoic Acid 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:

(2S,4R)-5-biphenyl-4-yl-2-methyl-2-(tetrahydropyran-2-yloxymethyl)-4-[(1H-1,2,3-triazole-4-carbonyl)amino]pentanoic acid (1562404-71-0) + isobutyryl chloride (79-30-1) → (2S,4R)-5-biphenyl-4-yl-2-isobutyryloxymethyl-2-methyl-4-[(3H-[1,2,3]triazole-4-carbonyl)amino]pentanoic Acid (1562404-16-3)

Guidance literature:

(2S,4R)-5-biphenyl-4-yl-2-methyl-2-(tetrahydropyran-2-yloxymethyl)-4-[(1H-1,2,3-triazole-4-carbonyl)amino]pentanoic acid; With hydrogenchloride; In 1,4-dioxane; acetonitrile;

isobutyryl chloride; With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 0.166667h;

Reference yield:

(2R)-3-(biphenyl-4-yl)-2-[(tert-butoxycarbonyl)amino]propanoic acid (128779-47-5) → (2S,4R)-5-biphenyl-4-yl-2-isobutyryloxymethyl-2-methyl-4-[(3H-[1,2,3]triazole-4-carbonyl)amino]pentanoic Acid (1562404-16-3)

Guidance literature:

Multi-step reaction with 13 steps

1.1: dmap / dichloromethane / 0.5 h / -5 °C / Inert atmosphere

1.2: -20 - 0 °C

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

2.2: 3 h / -5 °C

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

4.1: hydrogenchloride / 24 h / 0 - 23 °C

5.1: 4-methyl-morpholine / tetrahydrofuran / 0.33 h / 0 - 5 °C

6.1: sodium tetrahydroborate / water; tetrahydrofuran / 0.33 h / 0 °C

6.2: 1 h / 23 °C

7.1: toluene-4-sulfonic acid / dichloromethane / 2 h / 0 - 23 °C

8.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.75 h / 0 °C / Inert atmosphere

8.2: 1 h / 5 - 23 °C

9.1: water; lithium hydroxide / tetrahydrofuran / 5 - 35 °C

10.1: potassium carbonate / N,N-dimethyl-formamide / 0 - 23 °C

10.3: 0 - 10 °C

11.1: 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V); N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.25 h / 0 °C

11.2: 1.5 h / 0 - 23 °C

12.1: hydrogen; palladium 10% on activated carbon / ethyl acetate / 23 °C / Inert atmosphere

13.1: hydrogenchloride / 1,4-dioxane; acetonitrile

13.2: 0.17 h

With 4-methyl-morpholine; hydrogenchloride; dmap; sodium tetrahydroborate; 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V); palladium 10% on activated carbon; water; hydrogen; sodium hexamethyldisilazane; potassium carbonate; toluene-4-sulfonic acid; acetic acid; N-ethyl-N,N-diisopropylamine; lithium hydroxide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

Reference yield:

[(R)-1-(biphenyl-4-yl)-methyl-2-(2,2,5-trimethyl-4,6-dioxo-[1,3]dioxan-5-yl)-ethyl]-carbamic acid t-butyl ester (1394050-22-6) → (2S,4R)-5-biphenyl-4-yl-2-isobutyryloxymethyl-2-methyl-4-[(3H-[1,2,3]triazole-4-carbonyl)amino]pentanoic Acid (1562404-16-3)

Guidance literature:

Multi-step reaction with 10 steps

1.1: hydrogenchloride / 24 h / 0 - 23 °C

2.1: 4-methyl-morpholine / tetrahydrofuran / 0.33 h / 0 - 5 °C

3.1: sodium tetrahydroborate / water; tetrahydrofuran / 0.33 h / 0 °C

3.2: 1 h / 23 °C

4.1: toluene-4-sulfonic acid / dichloromethane / 2 h / 0 - 23 °C

5.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.75 h / 0 °C / Inert atmosphere

5.2: 1 h / 5 - 23 °C

6.1: water; lithium hydroxide / tetrahydrofuran / 5 - 35 °C

7.1: potassium carbonate / N,N-dimethyl-formamide / 0 - 23 °C

7.3: 0 - 10 °C

8.1: 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V); N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.25 h / 0 °C

8.2: 1.5 h / 0 - 23 °C

9.1: hydrogen; palladium 10% on activated carbon / ethyl acetate / 23 °C / Inert atmosphere

10.1: hydrogenchloride / 1,4-dioxane; acetonitrile

10.2: 0.17 h

With 4-methyl-morpholine; hydrogenchloride; sodium tetrahydroborate; 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V); palladium 10% on activated carbon; water; hydrogen; sodium hexamethyldisilazane; potassium carbonate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; lithium hydroxide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

upstream raw materials:

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

isobutyryl chloride

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

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