(R)-2-{3-[(N-benzyloxycarbonyl-(R)-pipecolyl-(S)-isoleucyl)methylamino]-4-methylpentyl}thiazole-4-carboxylic acid

Base Information

• Chemical Name: (R)-2-{3-[(N-benzyloxycarbonyl-(R)-pipecolyl-(S)-isoleucyl)methylamino]-4-methylpentyl}thiazole-4-carboxylic acid
• CAS No.: 1174764-22-7
• Molecular Formula: C₃₁H₄₄N₄O₆S
• Molecular Weight: 600.78
• Mol file: 1174764-22-7.mol

Synonyms:(R)-2-{3-[(N-benzyloxycarbonyl-(R)-pipecolyl-(S)-isoleucyl)methylamino]-4-methylpentyl}thiazole-4-carboxylic acid

Chemical Property of (R)-2-{3-[(N-benzyloxycarbonyl-(R)-pipecolyl-(S)-isoleucyl)methylamino]-4-methylpentyl}thiazole-4-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-{3-[(N-benzyloxycarbonyl-(R)-pipecolyl-(S)-isoleucyl)methylamino]-4-methylpentyl}thiazole-4-carboxylic acid

There total 11 articles about (R)-2-{3-[(N-benzyloxycarbonyl-(R)-pipecolyl-(S)-isoleucyl)methylamino]-4-methylpentyl}thiazole-4-carboxylic 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: 98.0%

ethyl (R)-2-{3-[(N-benzyloxycarbonyl-(R)-pipecolyl-(S)-isoleucyl)methylamino]-4-methylpentyl}thiazole-4-carboxylate (1174764-21-6) → (R)-2-{3-[(N-benzyloxycarbonyl-(R)-pipecolyl-(S)-isoleucyl)methylamino]-4-methylpentyl}thiazole-4-carboxylic acid (1174764-22-7)

Guidance literature:

ethyl (R)-2-{3-[(N-benzyloxycarbonyl-(R)-pipecolyl-(S)-isoleucyl)methylamino]-4-methylpentyl}thiazole-4-carboxylate; With sodium hydroxide; In 1,4-dioxane; at 0 ℃;

With hydrogenchloride; In water; pH=2;

DOI:10.1002/ejoc.200900999

Reference yield:

(4S,2E)-4-(tert-butoxycarbonylamino)-5-methyl-2-hexenenitrile (1207472-50-1) → (R)-2-{3-[(N-benzyloxycarbonyl-(R)-pipecolyl-(S)-isoleucyl)methylamino]-4-methylpentyl}thiazole-4-carboxylic acid (1174764-22-7)

Guidance literature:

Multi-step reaction with 9 steps

1.1: palladium 10% on activated carbon; hydrogen / methanol

2.1: sodium hydride / N,N-dimethyl-formamide / 0 - 20 °C

3.1: hydrogen sulfide; triethylamine / chloroform / -78 - 20 °C

4.1: acetone / 1.5 h / -10 °C

4.2: -20 - 0 °C

5.1: hydrogenchloride / 1,4-dioxane / 0 °C

6.1: 2-bromo-1-ethylpyridin-1-ium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / dichloromethane / -10 - 20 °C

7.1: hydrogen bromide / acetic acid / 0 °C

8.1: sodium hydrogencarbonate / water

8.2: -20 - 20 °C

9.1: sodium hydroxide / 1,4-dioxane / 0 °C

9.2: pH 2

With hydrogenchloride; palladium 10% on activated carbon; hydrogen sulfide; hydrogen bromide; hydrogen; 2-bromo-1-ethylpyridin-1-ium tetrafluoroborate; sodium hydride; sodium hydrogencarbonate; triethylamine; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In 1,4-dioxane; methanol; dichloromethane; chloroform; water; acetic acid; N,N-dimethyl-formamide; acetone; 4.1: Hantzsch thiazole synthesis;

DOI:10.1002/ejoc.200900999

Reference yield:

N-tert-butoxycarbonyl-L-valine methyl ester (58561-04-9) → (R)-2-{3-[(N-benzyloxycarbonyl-(R)-pipecolyl-(S)-isoleucyl)methylamino]-4-methylpentyl}thiazole-4-carboxylic acid (1174764-22-7)

Guidance literature:

Multi-step reaction with 11 steps

1.1: diisobutylaluminium hydride / hexae; toluene / 0.5 h / -78 °C

2.1: potassium tert-butylate / toluene / -78 - 20 °C

3.1: palladium 10% on activated carbon; hydrogen / methanol

4.1: sodium hydride / N,N-dimethyl-formamide / 0 - 20 °C

5.1: hydrogen sulfide; triethylamine / chloroform / -78 - 20 °C

6.1: acetone / 1.5 h / -10 °C

6.2: -20 - 0 °C

7.1: hydrogenchloride / 1,4-dioxane / 0 °C

8.1: 2-bromo-1-ethylpyridin-1-ium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / dichloromethane / -10 - 20 °C

9.1: hydrogen bromide / acetic acid / 0 °C

10.1: sodium hydrogencarbonate / water

10.2: -20 - 20 °C

11.1: sodium hydroxide / 1,4-dioxane / 0 °C

11.2: pH 2

With hydrogenchloride; palladium 10% on activated carbon; hydrogen sulfide; potassium tert-butylate; hydrogen bromide; hydrogen; 2-bromo-1-ethylpyridin-1-ium tetrafluoroborate; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; triethylamine; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In 1,4-dioxane; methanol; dichloromethane; chloroform; hexae; water; acetic acid; N,N-dimethyl-formamide; acetone; toluene; 2.1: Wittig reaction / 6.1: Hantzsch thiazole synthesis;

DOI:10.1002/ejoc.200900999

upstream raw materials:

(4R)-4-[(tert-butoxycarbonyl)methylamino]-5-methylhexanenitrile

(4R)-4-[(tert-butoxycarbonyl)methylamino]-5-methylhexanethioamide

(4S,2E)-4-(tert-butoxycarbonylamino)-5-methyl-2-hexenenitrile

ethyl (R)-2-{3-[(N-benzyloxycarbonyl-(R)-pipecolyl-(S)-isoleucyl)methylamino]-4-methylpentyl}thiazole-4-carboxylate

Downstream raw materials:

C₃₆H₅₅N₅O₅S

(4R)-4-[((R)-2-{3-[methyl-(N-methyl-(R)-pipecolyl-(S)-isoleucyl)-amino]-4-methyl-pentyl}-thiazole-4-carbonyl)-amino]-5-phenyl-pentanoic acid trifluoroacetic acid salt

methyl (2S,4R)-2-methyl-4-[({2-[(3R)-4-methyl-3-{methyl[(2S,3S)-3-methyl-2-({[(2R)-1-methylpiperidin-2-yl]carbonyl}amino)pentanoyl]amino}pentyl]-1,3-thiazol-4-yl}carbonyl)amino]-5-phenylpentanoate

(2S,4R)-4-[((R)-2-{3-[methyl-(N-methyl-(R)-pipecolyl-(S)-isoleucyl)-amino]-4-methyl-pentyl}-thiazole-4-carbonyl)-amino]-2-methyl-5-phenyl-pentanoic acid trifluoroacetic acid salt