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

Base Information

• Chemical Name: ethyl (R)-2-{3-[(N-benzyloxycarbonyl-(S)-isoleucyl)methylamino]-4-methylpentyl}thiazole-4-carboxylate
• CAS No.: 1174764-17-0
• Molecular Formula: C₂₇H₃₉N₃O₅S
• Molecular Weight: 517.69
• Mol file: 1174764-17-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about ethyl (R)-2-{3-[(N-benzyloxycarbonyl-(S)-isoleucyl)methylamino]-4-methylpentyl}thiazole-4-carboxylate 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: 88.0%

C13H22N2O2S + (2S,3S)-3-methyl-1-oxopentane-2-benzylcarbamate (149357-59-5) → ethyl (R)-2-{3-[(N-benzyloxycarbonyl-(S)-isoleucyl)methylamino]-4-methylpentyl}thiazole-4-carboxylate (1174764-17-0)

Guidance literature:

With 2-bromo-1-ethylpyridin-1-ium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 10 ℃;

Reference yield:

C13H22N2O2S*ClH + N-Cbz-L-Isoleucine (3160-59-6) → ethyl (R)-2-{3-[(N-benzyloxycarbonyl-(S)-isoleucyl)methylamino]-4-methylpentyl}thiazole-4-carboxylate (1174764-17-0)

Guidance literature:

With 2-bromo-1-ethylpyridin-1-ium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -10 - 20 ℃;

DOI:10.1002/ejoc.200900999

Reference yield:

N-tert-butoxycarbonyl-L-valine methyl ester (58561-04-9) → ethyl (R)-2-{3-[(N-benzyloxycarbonyl-(S)-isoleucyl)methylamino]-4-methylpentyl}thiazole-4-carboxylate (1174764-17-0)

Guidance literature:

Multi-step reaction with 8 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

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

DOI:10.1002/ejoc.200900999

upstream raw materials:

(2S,3S)-3-methyl-1-oxopentane-2-benzylcarbamate

(R)-ethyl 2-(3-((tert-butoxycarbonyl)(methyl)amino)-4-methylpentyl)thiazole-4-carboxylate

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

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

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

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