2-(1-azido-ethyl)-5-cyclohexylmethylsulfanyl-3-methyl-3H-imidazole-4-carboxylic acid ethyl ester

Base Information

• Chemical Name: 2-(1-azido-ethyl)-5-cyclohexylmethylsulfanyl-3-methyl-3H-imidazole-4-carboxylic acid ethyl ester
• CAS No.: 330438-39-6
• Molecular Formula: C₁₆H₂₅N₅O₂S
• Molecular Weight: 351.473

Synonyms:2-(1-azido-ethyl)-5-cyclohexylmethylsulfanyl-3-methyl-3H-imidazole-4-carboxylic acid ethyl ester

Chemical Property of 2-(1-azido-ethyl)-5-cyclohexylmethylsulfanyl-3-methyl-3H-imidazole-4-carboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

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Technology Process of 2-(1-azido-ethyl)-5-cyclohexylmethylsulfanyl-3-methyl-3H-imidazole-4-carboxylic acid ethyl ester

There total 10 articles about 2-(1-azido-ethyl)-5-cyclohexylmethylsulfanyl-3-methyl-3H-imidazole-4-carboxylic acid ethyl 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:

ethyl-2-aminocyano acetate (32683-02-6) → 2-(1-azido-ethyl)-5-cyclohexylmethylsulfanyl-3-methyl-3H-imidazole-4-carboxylic acid ethyl ester (330438-39-6)

Guidance literature:

Multi-step reaction with 11 steps

1: 62 percent / pyridine / tetrahydrofuran / 2 h

2: 84 percent / TEA / ethanol / 5 °C

3: 79 percent / propane phosphonic anhydride / ethyl acetate / 2 h / Heating

4: 90 percent / K₂CO₃ / dimethylformamide / 3 h

5: 89 percent / HCOCOOH; aq. AcOH; HCl / 30 h / 20 °C

6: 55 percent / tetrahydrofuran / 0.25 h / 0 °C

7: 85 percent / DPPA; DBU / toluene / 24 h

8: 85 percent / mCPBA / CH₂Cl₂ / 0.25 h / 0 °C

9: CH₂Cl₂ / 0.25 h

10: TEA; MeOH / 0.08 h

11: methanol / 20 °C

With pyridine; hydrogenchloride; methanol; TEA; propylphosphonic anhydride; diphenyl-phosphinic acid; potassium carbonate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; Glyoxilic acid; In tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; 9: Pummerer reaction;

DOI:10.1016/S0960-894X(02)00138-5

Reference yield:

2-formyl-3-methyl-5-methylsulfanyl-3H-imidazole-4-carboxylic acid ethyl ester (330438-34-1) → 2-(1-azido-ethyl)-5-cyclohexylmethylsulfanyl-3-methyl-3H-imidazole-4-carboxylic acid ethyl ester (330438-39-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 55 percent / tetrahydrofuran / 0.25 h / 0 °C

2: 85 percent / DPPA; DBU / toluene / 24 h

3: 85 percent / mCPBA / CH₂Cl₂ / 0.25 h / 0 °C

4: CH₂Cl₂ / 0.25 h

5: TEA; MeOH / 0.08 h

6: methanol / 20 °C

With methanol; TEA; diphenyl-phosphinic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; toluene; 4: Pummerer reaction;

DOI:10.1016/S0960-894X(02)00138-5

Reference yield:

2-(1-hydroxy-ethyl)-3-methyl-5-methylsulfanyl-3H-imidazole-4-carboxylic acid ethyl ester (330438-36-3) → 2-(1-azido-ethyl)-5-cyclohexylmethylsulfanyl-3-methyl-3H-imidazole-4-carboxylic acid ethyl ester (330438-39-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 85 percent / DPPA; DBU / toluene / 24 h

2: 85 percent / mCPBA / CH₂Cl₂ / 0.25 h / 0 °C

3: CH₂Cl₂ / 0.25 h

4: TEA; MeOH / 0.08 h

5: methanol / 20 °C

With methanol; TEA; diphenyl-phosphinic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane; toluene; 3: Pummerer reaction;

DOI:10.1016/S0960-894X(02)00138-5

upstream raw materials:

cyclohexylmethyl iodide

ethyl-2-aminocyano acetate

2-formyl-3-methyl-5-methylsulfanyl-3H-imidazole-4-carboxylic acid ethyl ester

2-(1-hydroxy-ethyl)-3-methyl-5-methylsulfanyl-3H-imidazole-4-carboxylic acid ethyl ester

Downstream raw materials:

2-(1-{2-acetylamino-3-[4-(bis-benzyloxy-phosphoryloxy)-phenyl]-propionylamino}-ethyl)-5-cyclohexylmethylsulfanyl-3-methyl-3H-imidazole-4-carboxylic acid ethyl ester

phosphoric acid 4-{2-acetylamino-2-[1-(5-carbamoyl-4-cyclohexylmethylsulfanyl-1-methyl-1H-imidazol-2-yl)-ethylcarbamoyl]-ethyl}-phenyl ester dibenzyl ester

2-(1-azido-ethyl)-5-cyclohexylmethylsulfanyl-3-methyl-3H-imidazole-4-carboxylic acid amide

2-(1-amino-ethyl)-5-cyclohexylmethylsulfanyl-3-methyl-3H-imidazole-4-carboxylic acid amide

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