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

Base Information

• Chemical Name: methyl (4R)-4-[((R)-2-{3-[(N,N-dimethylglycyl-(S)-isoleucyl)methylamino]-4-methylpentyl}thiazole-4-carbonyl)amino]-5-phenylpentanoate
• CAS No.: 1207472-54-5
• Molecular Formula: C₃₃H₅₁N₅O₅S
• Molecular Weight: 629.864
• Mol file: 1207472-54-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 17 articles about methyl (4R)-4-[((R)-2-{3-[(N,N-dimethylglycyl-(S)-isoleucyl)methylamino]-4-methylpentyl}thiazole-4-carbonyl)amino]-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:

(R)-ethyl 2-(3-((tert-butoxycarbonyl)(methyl)amino)-4-methylpentyl)thiazole-4-carboxylate (1053805-75-6) → methyl (4R)-4-[((R)-2-{3-[(N,N-dimethylglycyl-(S)-isoleucyl)methylamino]-4-methylpentyl}thiazole-4-carbonyl)amino]-5-phenylpentanoate (1207472-54-5)

Guidance literature:

Multi-step reaction with 7 steps

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

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

3: sodium hydroxide / 1,4-dioxane

4: 4-methyl-morpholine / tetrahydrofuran / 0.17 h / -20 °C

5: 4-methyl-morpholine / tetrahydrofuran / -20 - 20 °C

6: hydrogen bromide / acetic acid / 0 °C

7: dichloromethane

With 4-methyl-morpholine; hydrogenchloride; hydrogen bromide; 2-bromo-1-ethylpyridin-1-ium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; acetic acid;

DOI:10.1002/ejoc.200900999

Reference yield:

(4R)-4-(tert.-Butoxycarbonylamino)-5-methyl-hexanenitrile (1219930-72-9) → methyl (4R)-4-[((R)-2-{3-[(N,N-dimethylglycyl-(S)-isoleucyl)methylamino]-4-methylpentyl}thiazole-4-carbonyl)amino]-5-phenylpentanoate (1207472-54-5)

Guidance literature:

Multi-step reaction with 10 steps

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

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

3.1: acetone / 1.5 h / -10 °C

3.2: -20 - 0 °C

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

5.1: 2-bromo-1-ethylpyridin-1-ium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / dichloromethane / -10 - 20 °C

6.1: sodium hydroxide / 1,4-dioxane

7.1: 4-methyl-morpholine / tetrahydrofuran / 0.17 h / -20 °C

8.1: 4-methyl-morpholine / tetrahydrofuran / -20 - 20 °C

9.1: hydrogen bromide / acetic acid / 0 °C

10.1: dichloromethane

With 4-methyl-morpholine; hydrogenchloride; hydrogen sulfide; hydrogen bromide; 2-bromo-1-ethylpyridin-1-ium tetrafluoroborate; sodium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; chloroform; acetic acid; N,N-dimethyl-formamide; acetone; 3.1: Hantzsch thiazole synthesis;

DOI:10.1002/ejoc.200900999

Reference yield:

ethyl (R)-2-{3-[(N-benzyloxycarbonyl-(S)-isoleucyl)methylamino]-4-methylpentyl}thiazole-4-carboxylate (1174764-17-0) → methyl (4R)-4-[((R)-2-{3-[(N,N-dimethylglycyl-(S)-isoleucyl)methylamino]-4-methylpentyl}thiazole-4-carbonyl)amino]-5-phenylpentanoate (1207472-54-5)

Guidance literature:

Multi-step reaction with 5 steps

1: sodium hydroxide / 1,4-dioxane

2: 4-methyl-morpholine / tetrahydrofuran / 0.17 h / -20 °C

3: 4-methyl-morpholine / tetrahydrofuran / -20 - 20 °C

4: hydrogen bromide / acetic acid / 0 °C

5: dichloromethane

With 4-methyl-morpholine; hydrogen bromide; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; acetic acid;

DOI:10.1002/ejoc.200900999

upstream raw materials:

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

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

(4R)-4-(tert.-Butoxycarbonylamino)-5-methyl-hexanenitrile

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

Downstream raw materials:

(4R)-4-[((R)-2-{3-[(N,N-dimethylglycyl-(S)-isoleucyl)methylamino]-4-methylpentyl}thiazole-4-carboxyl)amino]-5-phenylpentanoic acid trifluoroacetic acid salt