4-({2-[1-acetoxy-3-(2-amino-3-methyl-pentanoylamino)-4-methyl-pentyl]-thiazole-4-carbonyl}-amino)-2-methyl-5-phenyl-pentanoic acid methyl ester

Base Information

• Chemical Name: 4-({2-[1-acetoxy-3-(2-amino-3-methyl-pentanoylamino)-4-methyl-pentyl]-thiazole-4-carbonyl}-amino)-2-methyl-5-phenyl-pentanoic acid methyl ester
• CAS No.: 943218-34-6
• Molecular Formula: C₃₁H₄₆N₄O₆S
• Molecular Weight: 602.795
• Mol file: 943218-34-6.mol

Synonyms:4-({2-[1-acetoxy-3-(2-amino-3-methyl-pentanoylamino)-4-methyl-pentyl]-thiazole-4-carbonyl}-amino)-2-methyl-5-phenyl-pentanoic acid methyl ester

Chemical Property of 4-({2-[1-acetoxy-3-(2-amino-3-methyl-pentanoylamino)-4-methyl-pentyl]-thiazole-4-carbonyl}-amino)-2-methyl-5-phenyl-pentanoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-({2-[1-acetoxy-3-(2-amino-3-methyl-pentanoylamino)-4-methyl-pentyl]-thiazole-4-carbonyl}-amino)-2-methyl-5-phenyl-pentanoic acid methyl ester

There total 19 articles about 4-({2-[1-acetoxy-3-(2-amino-3-methyl-pentanoylamino)-4-methyl-pentyl]-thiazole-4-carbonyl}-amino)-2-methyl-5-phenyl-pentanoic acid methyl ester 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: 93.0%

4-({2-[1-acetoxy-3-(2-benzyloxycarbonylamino-3-methyl-pentanoylamino)-4-methyl-pentyl]-thiazole-4-carbonyl}-amino)-2-methyl-5-phenyl-pentanoic acid methyl ester (919518-65-3) → 4-({2-[1-acetoxy-3-(2-amino-3-methyl-pentanoylamino)-4-methyl-pentyl]-thiazole-4-carbonyl}-amino)-2-methyl-5-phenyl-pentanoic acid methyl ester (943218-34-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol;

DOI:10.1002/anie.200601259

Reference yield:

4-({2-[3-(2-benzyloxycarbonylamino-3-methyl-pentanoylamino)-1-hydroxy-4-methyl-pentyl]-thiazole-4-carbonyl}-amino)-2-methyl-5-phenyl-pentanoic acid methyl ester → 4-({2-[1-acetoxy-3-(2-amino-3-methyl-pentanoylamino)-4-methyl-pentyl]-thiazole-4-carbonyl}-amino)-2-methyl-5-phenyl-pentanoic acid methyl ester (943218-34-6)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 3 h / 20 °C

2: 93 percent / H₂ / Pd/C / methanol

With pyridine; hydrogen; palladium on activated charcoal; In methanol;

DOI:10.1002/anie.200601259

Reference yield:

5-benzyl-3-methylenepyrrolidin-2-one → 4-({2-[1-acetoxy-3-(2-amino-3-methyl-pentanoylamino)-4-methyl-pentyl]-thiazole-4-carbonyl}-amino)-2-methyl-5-phenyl-pentanoic acid methyl ester (943218-34-6)

Guidance literature:

Multi-step reaction with 10 steps

1.1: triethylamine; dmap / dichloromethane / 24 h / 20 °C

2.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 24 h / 20 °C / 760.05 Torr

3.1: lithium hydroxide; water / tetrahydrofuran / 3 h / 20 °C

4.1: diethyl ether / 20 °C

5.1: trifluoroacetic acid / dichloromethane / 4 h / 20 °C / Cooling with ice

6.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; 1-hydroxy-7-aza-benzotriazole / N,N-dimethyl-formamide / 0.08 h

6.2: 24 h / 0 - 20 °C

7.1: pyridine / 12 h

8.1: hydrogenchloride / 1,4-dioxane / 2 h / 0 °C

9.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 0 °C

10.1: hydrogenchloride / 1,4-dioxane / 2 h / Cooling with ice

With pyridine; hydrogenchloride; dmap; 1-hydroxy-7-aza-benzotriazole; palladium 10% on activated carbon; water; hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; lithium hydroxide; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1002/cjoc.201200984

upstream raw materials:

4-({2-[1-acetoxy-3-(2-benzyloxycarbonylamino-3-methyl-pentanoylamino)-4-methyl-pentyl]-thiazole-4-carbonyl}-amino)-2-methyl-5-phenyl-pentanoic acid methyl ester

(S)-2-methyl N-((R)-2-methylhex-5-en-3-yl)propane-2-sulfinamide

(R)-tert-butyl (2-methylhex-5-en-3-yl)carbamate

methyl 2-{(1R,3R)-1-acetoxy-3-[(tert-butoxycarbonyl)amino]-4-methylpentyl}-1,3-thiazole-4-carboxylate

Downstream raw materials:

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

C₃₇H₅₅N₅O₇S

(R)-benzyl 2-((2S,3S)-1-((1R,3R)-1-acetoxy-1-(4-((2R,4S)-5-methoxy-4-methyl-5-oxo-1-phenylpentan-2-ylcarbamoyl)thiazol-2-yl)-4-methylpentan-3-ylamino)-3-methyl-1-oxopentan-2-ylcarbamoyl)piperidine-1-carboxylate