3-benzyl-4-undecyloxazolidine-2,5-dione

Base Information

• Chemical Name: 3-benzyl-4-undecyloxazolidine-2,5-dione
• CAS No.: 444023-47-6
• Molecular Formula: C₂₁H₃₁NO₃
• Molecular Weight: 345.482
• Mol file: 444023-47-6.mol

Synonyms:3-benzyl-4-undecyloxazolidine-2,5-dione

Chemical Property of 3-benzyl-4-undecyloxazolidine-2,5-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-benzyl-4-undecyloxazolidine-2,5-dione

There total 13 articles about 3-benzyl-4-undecyloxazolidine-2,5-dione 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: 78.0%

(+/-)-1-benzyl-3-oxo-4-undecyl-2-azetidinone (444023-43-2) → 3-benzyl-4-undecyloxazolidine-2,5-dione (444023-47-6)

Guidance literature:

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; potassium bromide; In phosphate buffer; dichloromethane; at 0 ℃; for 1h; pH=6.9;

DOI:10.1021/jo0162437

Reference yield:

lauric acid (143-07-7) → 3-benzyl-4-undecyloxazolidine-2,5-dione (444023-47-6)

Guidance literature:

Multi-step reaction with 13 steps

1.1: tetrahydrofuran / 0 - 20 °C

2.1: 14.72 g / 72 h / 20 °C

3.1: 86 percent / sodium borohydride / methanol / 0 °C

4.1: 85 percent / AlMe₃ / CH₂Cl₂; heptane / 0 - 20 °C

5.1: 84 percent / triphenylphosphine; carbon tetrachloride; triethylamine / acetonitrile / 0 - 20 °C

6.1: H₂ / Pd/C / methanol

7.1: 90 percent / diisopropylethylamine / acetonitrile / 0.5 h / 0 °C

8.1: 65 percent / trimethylsilyl azide; diisopropylethylamine / acetonitrile / 20 °C

9.1: 66 percent / CsF / dimethylformamide

10.1: H₂ / 10percent Pd/C / tetrahydrofuran / 0.33 h / 760.05 Torr

11.1: tert-butyl hypochlorite / tetrahydrofuran / 0.33 h / -78 °C

12.1: DBU / tetrahydrofuran / 1.5 h / -78 - 20 °C

12.2: 27 mg / oxalic acid / tetrahydrofuran; H₂O / 0.17 h / 20 °C

13.1: 78 percent / TEMPO; NaOCl; KBr / CH₂Cl₂; aq. phosphate buffer / 1 h / 0 °C / pH 6.9

With tetrachloromethane; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium tetrahydroborate; tert-butylhypochlorite; trimethylsilylazide; hydrogen; trimethylaluminum; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; cesium fluoride; potassium bromide; palladium on activated charcoal; In tetrahydrofuran; methanol; phosphate buffer; n-heptane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo0162437

Reference yield:

methyl 3-oxotetradecanoate (22348-97-6) → 3-benzyl-4-undecyloxazolidine-2,5-dione (444023-47-6)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 86 percent / sodium borohydride / methanol / 0 °C

2.1: 85 percent / AlMe₃ / CH₂Cl₂; heptane / 0 - 20 °C

3.1: 84 percent / triphenylphosphine; carbon tetrachloride; triethylamine / acetonitrile / 0 - 20 °C

4.1: H₂ / Pd/C / methanol

5.1: 90 percent / diisopropylethylamine / acetonitrile / 0.5 h / 0 °C

6.1: 65 percent / trimethylsilyl azide; diisopropylethylamine / acetonitrile / 20 °C

7.1: 66 percent / CsF / dimethylformamide

8.1: H₂ / 10percent Pd/C / tetrahydrofuran / 0.33 h / 760.05 Torr

9.1: tert-butyl hypochlorite / tetrahydrofuran / 0.33 h / -78 °C

10.1: DBU / tetrahydrofuran / 1.5 h / -78 - 20 °C

10.2: 27 mg / oxalic acid / tetrahydrofuran; H₂O / 0.17 h / 20 °C

11.1: 78 percent / TEMPO; NaOCl; KBr / CH₂Cl₂; aq. phosphate buffer / 1 h / 0 °C / pH 6.9

With tetrachloromethane; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium tetrahydroborate; tert-butylhypochlorite; trimethylsilylazide; hydrogen; trimethylaluminum; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; cesium fluoride; potassium bromide; palladium on activated charcoal; In tetrahydrofuran; methanol; phosphate buffer; n-heptane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo0162437

upstream raw materials:

(+/-)-1-benzyl-3-oxo-4-undecyl-2-azetidinone

lauric acid

methyl 3-oxotetradecanoate

(+/-)-3-hydroxytetradecanoic acid methyl ester

Refernces