Pentanamide, 2-(dimethylamino)-3-methyl-N-(3-(1-methylethyl)-7-(2-methylpropyl)-5,8-dioxo-2-oxa-6,9-diazabicyclo(10.2.2)hexadeca-10,12,14,15-tetraen-4-yl)-, (3R-(3R*,4S*(2S*,3S*),7S*))-

Base Information

• Chemical Name: Pentanamide, 2-(dimethylamino)-3-methyl-N-(3-(1-methylethyl)-7-(2-methylpropyl)-5,8-dioxo-2-oxa-6,9-diazabicyclo(10.2.2)hexadeca-10,12,14,15-tetraen-4-yl)-, (3R-(3R*,4S*(2S*,3S*),7S*))-
• CAS No.: 25350-22-5
• Molecular Formula: C₂₈H₄₄N₄O₄
• Molecular Weight: 500.682
• Wikidata: Q105275287
• Mol file: 25350-22-5.mol

Synonyms:frangulanine

Chemical Property of Pentanamide, 2-(dimethylamino)-3-methyl-N-(3-(1-methylethyl)-7-(2-methylpropyl)-5,8-dioxo-2-oxa-6,9-diazabicyclo(10.2.2)hexadeca-10,12,14,15-tetraen-4-yl)-, (3R-(3R*,4S*(2S*,3S*),7S*))-

Chemical Property:

• Vapor Pressure: 4.09E-21mmHg at 25°C
• Boiling Point: 729.1°Cat760mmHg
• PKA: 13.27±0.60(Predicted)
• Flash Point: 394.7°C
• Density: 1.1g/cm³
• XLogP3: 5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 500.33625590
• Heavy Atom Count: 36
• Complexity: 759

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C)C(C(=O)NC1C(OC2=CC=C(C=C2)C=CNC(=O)C(NC1=O)CC(C)C)C(C)C)N(C)C
• Isomeric SMILES: CC[C@@H](C)[C@@H](C(=O)N[C@H]1[C@@H](OC2=CC=C(C=C2)/C=C\NC(=O)[C@@H](NC1=O)CC(C)C)C(C)C)N(C)C

Technology Process of Pentanamide, 2-(dimethylamino)-3-methyl-N-(3-(1-methylethyl)-7-(2-methylpropyl)-5,8-dioxo-2-oxa-6,9-diazabicyclo(10.2.2)hexadeca-10,12,14,15-tetraen-4-yl)-, (3R-(3R*,4S*(2S*,3S*),7S*))-

There total 24 articles about Pentanamide, 2-(dimethylamino)-3-methyl-N-(3-(1-methylethyl)-7-(2-methylpropyl)-5,8-dioxo-2-oxa-6,9-diazabicyclo(10.2.2)hexadeca-10,12,14,15-tetraen-4-yl)-, (3R-(3R*,4S*(2S*,3S*),7S*))- 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:

Z-L-leucine hydroxysuccinimide ester (3397-35-1) → frangulanine (25350-22-5,18658-41-8)

Guidance literature:

Multi-step reaction with 8 steps

1: KHCO₃ / dioxane / 14 h / 20 °C

2: 100 percent / Bu₄N⁺*F^- / dimethylformamide / 2 h / 20 °C

3: 91 percent / DCC / CH₂Cl₂ / 14 h / -20 - 20 °C

4: 44 percent / 4-pyrrolidinopyridine, H₂ / Pd/C / dioxane; 2-methyl-propan-2-ol / 40 h / 90 °C

5: Bu₃P / tetrahydrofuran / 3 h / 20 °C

6: 85 percent / H₂O₂, pyridine / CH₂Cl₂ / 1 h / 20 °C

7: CF₃CO₂H / various solvent(s) / 1 h / 0 °C

8: CH₂Cl₂ / 14 h / 20 °C

With pyridine; tributylphosphine; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; potassium hydrogencarbonate; 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1039/c39910001002

Reference yield:

(R)-4-((S)-1-Hydroxy-2-methyl-propyl)-oxazolidin-2-one (136983-35-2) → frangulanine (25350-22-5,18658-41-8)

Guidance literature:

Multi-step reaction with 19 steps

1: 71 percent / pyridine / 72 h / -10 - 20 °C

2: 93 percent / hexamethylphosphoric acid triamide / 5 h / 90 °C

3: 100 percent / 4-dimethylaminopyridine (DMAP), Et₃N / tetrahydrofuran / 4 h / 20 °C

4: 87 percent / Cs₂CO₃ / methanol / 5 h / 20 °C

5: pyridinium dichromate (PDC) / dimethylformamide / 40 h / 20 °C

6: DMAP, cyclohexylcarbodiimide (DCC) / diethyl ether / 20 h / -20 - 20 °C

7: 100 percent / 6 M HCl / dioxane / 5 h / 0 - 20 °C

8: 88 percent / NaHCO₃ / dioxane / 4 h / 20 °C

9: 1.) carbonyldiimidazole (Im₂CO), NaHCO₃ / 1.) THF, 20 deg C, 4 h, 2.) a) 50 deg C, 4 h, b) 20 deg C, 14 h

10: 79 percent / NaNO₂, aq. AcOH / 4 h / 0 °C

11: H₂, AcOH / Pd/C / 16 h / 20 °C

12: KHCO₃ / dioxane / 14 h / 20 °C

13: 100 percent / Bu₄N⁺*F^- / dimethylformamide / 2 h / 20 °C

14: 91 percent / DCC / CH₂Cl₂ / 14 h / -20 - 20 °C

15: 44 percent / 4-pyrrolidinopyridine, H₂ / Pd/C / dioxane; 2-methyl-propan-2-ol / 40 h / 90 °C

16: Bu₃P / tetrahydrofuran / 3 h / 20 °C

17: 85 percent / H₂O₂, pyridine / CH₂Cl₂ / 1 h / 20 °C

18: CF₃CO₂H / various solvent(s) / 1 h / 0 °C

19: CH₂Cl₂ / 14 h / 20 °C

With pyridine; hydrogenchloride; dmap; dipyridinium dichromate; tributylphosphine; N-cyclohexylcarbodiimide; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; sodium hydrogencarbonate; potassium hydrogencarbonate; caesium carbonate; 4-pyrrolidin-1-ylpyridine; acetic acid; triethylamine; dicyclohexyl-carbodiimide; 1,1'-carbonyldiimidazole; trifluoroacetic acid; sodium nitrite; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1039/c39910001002

Reference yield:

2,2,2-Trichloro-acetimidic acid (2S,3S)-3-isopropyl-oxiranylmethyl ester (136983-33-0) → frangulanine (25350-22-5,18658-41-8)

Guidance literature:

Multi-step reaction with 23 steps

1: 86 percent / CoCl₂ / acetonitrile / 14 h / 20 °C

2: NaHCO₃ / dioxane / 12 h / 20 °C

3: 86 percent / pyridine / 24 h / -10 - 20 °C

4: 78 percent / dioxane / 16 h / 100 °C

5: 71 percent / pyridine / 72 h / -10 - 20 °C

6: 93 percent / hexamethylphosphoric acid triamide / 5 h / 90 °C

7: 100 percent / 4-dimethylaminopyridine (DMAP), Et₃N / tetrahydrofuran / 4 h / 20 °C

8: 87 percent / Cs₂CO₃ / methanol / 5 h / 20 °C

9: pyridinium dichromate (PDC) / dimethylformamide / 40 h / 20 °C

10: DMAP, cyclohexylcarbodiimide (DCC) / diethyl ether / 20 h / -20 - 20 °C

11: 100 percent / 6 M HCl / dioxane / 5 h / 0 - 20 °C

12: 88 percent / NaHCO₃ / dioxane / 4 h / 20 °C

13: 1.) carbonyldiimidazole (Im₂CO), NaHCO₃ / 1.) THF, 20 deg C, 4 h, 2.) a) 50 deg C, 4 h, b) 20 deg C, 14 h

14: 79 percent / NaNO₂, aq. AcOH / 4 h / 0 °C

15: H₂, AcOH / Pd/C / 16 h / 20 °C

16: KHCO₃ / dioxane / 14 h / 20 °C

17: 100 percent / Bu₄N⁺*F^- / dimethylformamide / 2 h / 20 °C

18: 91 percent / DCC / CH₂Cl₂ / 14 h / -20 - 20 °C

19: 44 percent / 4-pyrrolidinopyridine, H₂ / Pd/C / dioxane; 2-methyl-propan-2-ol / 40 h / 90 °C

20: Bu₃P / tetrahydrofuran / 3 h / 20 °C

21: 85 percent / H₂O₂, pyridine / CH₂Cl₂ / 1 h / 20 °C

22: CF₃CO₂H / various solvent(s) / 1 h / 0 °C

23: CH₂Cl₂ / 14 h / 20 °C

With pyridine; hydrogenchloride; dmap; dipyridinium dichromate; tributylphosphine; N-cyclohexylcarbodiimide; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; sodium hydrogencarbonate; potassium hydrogencarbonate; caesium carbonate; 4-pyrrolidin-1-ylpyridine; acetic acid; triethylamine; dicyclohexyl-carbodiimide; 1,1'-carbonyldiimidazole; trifluoroacetic acid; sodium nitrite; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;

DOI:10.1039/c39910001002

upstream raw materials:

(Z)-(3S,4S,7S)-4-Amino-7-isobutyl-3-isopropyl-2-oxa-6,9-diaza-bicyclo[10.2.2]hexadeca-1⁽¹⁵⁾,10,12⁽¹⁶⁾,13-tetraene-5,8-dione

Z-L-leucine hydroxysuccinimide ester

(R)-4-((S)-1-Hydroxy-2-methyl-propyl)-oxazolidin-2-one

2,2,2-Trichloro-acetimidic acid (2S,3S)-3-isopropyl-oxiranylmethyl ester