3(R)-[3(S)-(N-Methylcarbamoyl)hexahydropyridazin-2-ylcarbonyl]dodecanehydroxamic acid

Base Information

• Chemical Name: 3(R)-[3(S)-(N-Methylcarbamoyl)hexahydropyridazin-2-ylcarbonyl]dodecanehydroxamic acid
• CAS No.: 163388-94-1
• Molecular Formula: C₁₉H₃₆N₄O₄
• Molecular Weight: 384.519
• Mol file: 163388-94-1.mol

Synonyms:

Chemical Property of 3(R)-[3(S)-(N-Methylcarbamoyl)hexahydropyridazin-2-ylcarbonyl]dodecanehydroxamic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3(R)-[3(S)-(N-Methylcarbamoyl)hexahydropyridazin-2-ylcarbonyl]dodecanehydroxamic acid

There total 14 articles about 3(R)-[3(S)-(N-Methylcarbamoyl)hexahydropyridazin-2-ylcarbonyl]dodecanehydroxamic 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:

(S)-2-[(R)-2-(Benzyloxycarbamoyl-methyl)-undecanoyl]-3-methylcarbamoyl-tetrahydro-pyridazine-1-carboxylic acid benzyl ester (163389-13-7) → N-methyl-(3S)-2-<(2R)-2-hydroxyaminocarbonylmethyl-1-oxoundecyl>hexahydropyridazine-3-carboxamide (163388-94-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 2.5h; Ambient temperature;

DOI:10.1248/cpb.43.1883

Reference yield:

undecanoyl chloride (17746-05-3) → N-methyl-(3S)-2-<(2R)-2-hydroxyaminocarbonylmethyl-1-oxoundecyl>hexahydropyridazine-3-carboxamide (163388-94-1)

Guidance literature:

Multi-step reaction with 14 steps

1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 25 min, 2.) THF, hexane, -78 deg C, 2.5 h

2: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 15 min, 2.) THF, from -78 deg C to -68 deg C, 3.5 h

3: 91 percent / tetrahydrofuran / 1 h / 0 °C

4: 100 percent / 3 N aq. HCl / dioxane / Ambient temperature

5: oxalyl chloride / toluene / 2 h / 60 °C

6: pyridine / 2.5 h / 0 °C

7: 81 percent / H₂ / 10percent Pd/C / methanol / 1.5 h / Ambient temperature

8: oxalyl chloride / benzene / 2 h / 60 °C

9: N-ethylmorpholine / tetrahydrofuran / -15 - 20 °C

10: Zn, 1 M aq. (NH₄)OAc / tetrahydrofuran / 3 h / Ambient temperature

11: triethylamine, diethylphosphoryl cyanide / tetrahydrofuran; dimethylformamide / 3.5 h / -15 °C

12: trifluoroacetic acid / CH₂Cl₂ / Ambient temperature

13: triethylamine, diethylphosphoryl cyanide / tetrahydrofuran; dimethylformamide / 4.5 h / -15 °C

14: H₂ / 10percent Pd/C / methanol / 2.5 h / Ambient temperature

With N-ethylmorpholine;; pyridine; hydrogenchloride; n-butyllithium; diethylphosphoryl cyanide; oxalyl dichloride; ammonium acetate; hydrogen; triethylamine; trifluoroacetic acid; zinc; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1248/cpb.43.1883

Reference yield:

(4S)-4-isopropyl-3-<(2R)-2-1-oxoundecyl>-2-oxazolidinone (163389-05-7) → N-methyl-(3S)-2-<(2R)-2-hydroxyaminocarbonylmethyl-1-oxoundecyl>hexahydropyridazine-3-carboxamide (163388-94-1)

Guidance literature:

Multi-step reaction with 13 steps

1: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 15 min, 2.) THF, from -78 deg C to -68 deg C, 3.5 h

2: 91 percent / tetrahydrofuran / 1 h / 0 °C

3: 100 percent / 3 N aq. HCl / dioxane / Ambient temperature

4: oxalyl chloride / toluene / 2 h / 60 °C

5: pyridine / 2.5 h / 0 °C

6: 81 percent / H₂ / 10percent Pd/C / methanol / 1.5 h / Ambient temperature

7: oxalyl chloride / benzene / 2 h / 60 °C

8: N-ethylmorpholine / tetrahydrofuran / -15 - 20 °C

9: Zn, 1 M aq. (NH₄)OAc / tetrahydrofuran / 3 h / Ambient temperature

10: triethylamine, diethylphosphoryl cyanide / tetrahydrofuran; dimethylformamide / 3.5 h / -15 °C

11: trifluoroacetic acid / CH₂Cl₂ / Ambient temperature

12: triethylamine, diethylphosphoryl cyanide / tetrahydrofuran; dimethylformamide / 4.5 h / -15 °C

13: H₂ / 10percent Pd/C / methanol / 2.5 h / Ambient temperature

With N-ethylmorpholine;; pyridine; hydrogenchloride; diethylphosphoryl cyanide; oxalyl dichloride; ammonium acetate; hydrogen; triethylamine; trifluoroacetic acid; zinc; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1248/cpb.43.1883

upstream raw materials:

(S)-2-[(R)-2-(Benzyloxycarbamoyl-methyl)-undecanoyl]-3-methylcarbamoyl-tetrahydro-pyridazine-1-carboxylic acid benzyl ester

undecanoyl chloride

(4S)-4-isopropyl-3-<(2R)-2-1-oxoundecyl>-2-oxazolidinone

(R)-3-Chlorocarbonyl-dodecanoic acid 2,2,2-trichloro-ethyl ester