methyl (2S,4R)-4-[((R)-2-{3-[(N-benzyloxycarbonyl-(R)-pipecolyl-(S)-isoleucyl)methylamino]-4-methylpentyl}thiazole-4-carbonyl)amino]-2-methyl-5-phenylpentanoate

Base Information

• Chemical Name: methyl (2S,4R)-4-[((R)-2-{3-[(N-benzyloxycarbonyl-(R)-pipecolyl-(S)-isoleucyl)methylamino]-4-methylpentyl}thiazole-4-carbonyl)amino]-2-methyl-5-phenylpentanoate
• CAS No.: 1207472-58-9
• Molecular Formula: C₄₄H₆₁N₅O₇S
• Molecular Weight: 804.064
• Mol file: 1207472-58-9.mol

Synonyms:methyl (2S,4R)-4-[((R)-2-{3-[(N-benzyloxycarbonyl-(R)-pipecolyl-(S)-isoleucyl)methylamino]-4-methylpentyl}thiazole-4-carbonyl)amino]-2-methyl-5-phenylpentanoate

Chemical Property of methyl (2S,4R)-4-[((R)-2-{3-[(N-benzyloxycarbonyl-(R)-pipecolyl-(S)-isoleucyl)methylamino]-4-methylpentyl}thiazole-4-carbonyl)amino]-2-methyl-5-phenylpentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2S,4R)-4-[((R)-2-{3-[(N-benzyloxycarbonyl-(R)-pipecolyl-(S)-isoleucyl)methylamino]-4-methylpentyl}thiazole-4-carbonyl)amino]-2-methyl-5-phenylpentanoate

There total 20 articles about methyl (2S,4R)-4-[((R)-2-{3-[(N-benzyloxycarbonyl-(R)-pipecolyl-(S)-isoleucyl)methylamino]-4-methylpentyl}thiazole-4-carbonyl)amino]-2-methyl-5-phenylpentanoate 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: 80.0%

(2S,4R)-methyl 4-amino-2-methyl-5-phenylpentanoate hydrochloride + (R)-2-{3-[(N-benzyloxycarbonyl-(R)-pipecolyl-(S)-isoleucyl)methylamino]-4-methylpentyl}thiazole-4-carboxylic acid (1174764-22-7) → methyl (2S,4R)-4-[((R)-2-{3-[(N-benzyloxycarbonyl-(R)-pipecolyl-(S)-isoleucyl)methylamino]-4-methylpentyl}thiazole-4-carbonyl)amino]-2-methyl-5-phenylpentanoate (1207472-58-9)

Guidance literature:

(R)-2-{3-[(N-benzyloxycarbonyl-(R)-pipecolyl-(S)-isoleucyl)methylamino]-4-methylpentyl}thiazole-4-carboxylic acid; With 4-methyl-morpholine; isobutyl chloroformate; In tetrahydrofuran; at -20 ℃; for 0.166667h;

methyl (2S,4R)-4-amino-2-methyl-5-phenylpentanoate hydrochloride; With 4-methyl-morpholine; In tetrahydrofuran; at -20 - 20 ℃;

Reference yield:

(4S,2E)-4-(tert-butoxycarbonylamino)-5-methyl-2-hexenenitrile (1207472-50-1) → methyl (2S,4R)-4-[((R)-2-{3-[(N-benzyloxycarbonyl-(R)-pipecolyl-(S)-isoleucyl)methylamino]-4-methylpentyl}thiazole-4-carbonyl)amino]-2-methyl-5-phenylpentanoate (1207472-58-9)

Guidance literature:

Multi-step reaction with 11 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

10.1: 4-methyl-morpholine / tetrahydrofuran / 0.17 h

11.1: 4-methyl-morpholine / tetrahydrofuran / -20 - 20 °C

With 4-methyl-morpholine; 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 tetrahydrofuran; 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) → methyl (2S,4R)-4-[((R)-2-{3-[(N-benzyloxycarbonyl-(R)-pipecolyl-(S)-isoleucyl)methylamino]-4-methylpentyl}thiazole-4-carbonyl)amino]-2-methyl-5-phenylpentanoate (1207472-58-9)

Guidance literature:

Multi-step reaction with 13 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

12.1: 4-methyl-morpholine / tetrahydrofuran / 0.17 h

13.1: 4-methyl-morpholine / tetrahydrofuran / -20 - 20 °C

With 4-methyl-morpholine; 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 tetrahydrofuran; 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

(S,E)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 4-((tert-butoxycarbonyl)amino)-2-methyl-5-phenylpent-2-enoate

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

Downstream raw materials:

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