(R)-3-(cyclopentylmethyl)-4-(cyclopropyl(4-(2-(6-methoxypyridin-3-yl)phenyl)thiazol-2-yl)amino)-4-oxobutanoic acid

Base Information

• Chemical Name: (R)-3-(cyclopentylmethyl)-4-(cyclopropyl(4-(2-(6-methoxypyridin-3-yl)phenyl)thiazol-2-yl)amino)-4-oxobutanoic acid
• CAS No.: 1229363-89-6
• Molecular Formula: C₂₈H₃₁N₃O₄S
• Molecular Weight: 505.638

Synonyms:(R)-3-(cyclopentylmethyl)-4-(cyclopropyl(4-(2-(6-methoxypyridin-3-yl)phenyl)thiazol-2-yl)amino)-4-oxobutanoic acid

Chemical Property of (R)-3-(cyclopentylmethyl)-4-(cyclopropyl(4-(2-(6-methoxypyridin-3-yl)phenyl)thiazol-2-yl)amino)-4-oxobutanoic acid

Chemical Property:

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Technology Process of (R)-3-(cyclopentylmethyl)-4-(cyclopropyl(4-(2-(6-methoxypyridin-3-yl)phenyl)thiazol-2-yl)amino)-4-oxobutanoic acid

There total 10 articles about (R)-3-(cyclopentylmethyl)-4-(cyclopropyl(4-(2-(6-methoxypyridin-3-yl)phenyl)thiazol-2-yl)amino)-4-oxobutanoic 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: 86.0%

tert-butyl (R)-3-(cyclopentylmethyl)-4-(cyclopropyl(4-(2-(6-methoxypyridin-3-yl)phenyl) thiazol-2-yl)amino)-4-oxobutanoate → (R)-3-(cyclopentylmethyl)-4-(cyclopropyl(4-(2-(6-methoxypyridin-3-yl)phenyl)thiazol-2-yl)amino)-4-oxobutanoic acid (1229363-89-6)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.1016/j.bmc.2018.09.015

Reference yield:

2,2'-dibromoacetophenone (49851-55-0) → (R)-3-(cyclopentylmethyl)-4-(cyclopropyl(4-(2-(6-methoxypyridin-3-yl)phenyl)thiazol-2-yl)amino)-4-oxobutanoic acid (1229363-89-6)

Guidance literature:

Multi-step reaction with 4 steps

1: ethanol / 2 h / Inert atmosphere; Reflux

2: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium carbonate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / toluene / 1.5 h / 85 °C / Inert atmosphere

3: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / acetonitrile / 60 °C / Inert atmosphere

4: trifluoroacetic acid / dichloromethane / 20 °C / Inert atmosphere

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium carbonate; 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; In ethanol; dichloromethane; toluene; acetonitrile; 1: |Hantzsch Thiazole Synthesis / 2: |Suzuki Coupling;

DOI:10.1016/j.bmc.2018.09.015

Reference yield:

2-methoxy-pyridine-5-boronic acid (163105-89-3,600726-67-8) → (R)-3-(cyclopentylmethyl)-4-(cyclopropyl(4-(2-(6-methoxypyridin-3-yl)phenyl)thiazol-2-yl)amino)-4-oxobutanoic acid (1229363-89-6)

Guidance literature:

Multi-step reaction with 3 steps

1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium carbonate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / toluene / 1.5 h / 85 °C / Inert atmosphere

2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / acetonitrile / 60 °C / Inert atmosphere

3: trifluoroacetic acid / dichloromethane / 20 °C / Inert atmosphere

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium carbonate; 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; In dichloromethane; toluene; acetonitrile; 1: |Suzuki Coupling;

DOI:10.1016/j.bmc.2018.09.015

upstream raw materials:

3-cyclopentylpropionic acid

2-bromophenyl methyl ketone

2,2'-dibromoacetophenone

2-methoxy-pyridine-5-boronic acid

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