(6S)-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine

Base Information

• Chemical Name: (6S)-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine
• CAS No.: 1131005-00-9
• Molecular Formula: C₁₄H₁₃F₃N₂O₃
• Molecular Weight: 314.264
• Mol file: 1131005-00-9.mol

Synonyms:(6S)-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine

Chemical Property of (6S)-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6S)-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine

There total 5 articles about (6S)-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine 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:

(6S)-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-ol (1105632-61-8) + 4-trifluoromethoxybenzyl bromide (50824-05-0) → (6S)-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (1131005-00-9)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide; mineral oil; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1021/jm801246z

Reference yield:

(S)-1-((tert-butyldimethylsilyl)oxy)-3-(2-nitro-1H-imidazol-1-yl)propan-2-ol (1162674-93-2) → (6S)-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (1131005-00-9)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridinium p-toluenesulfonate / dichloromethane / 16 h / 20 °C

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 15 h / 125 °C / Microwave irradiation

3: acetic acid / tetrahydrofuran; water / 16 h / 60 °C

4: sodium hydride; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide; mineral oil / 16 h / -50 - 20 °C

With tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;

DOI:10.1128/AAC.00722-13

Reference yield:

1-((2S)-3-((tert-butyldimethylsilyl)oxy)-2-((tetrahydro-2H-pyran-2-yl)oxy)propyl)-2-nitro-1H-imidazole (1105632-78-7) → (6S)-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (1131005-00-9)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 15 h / 125 °C / Microwave irradiation

2: acetic acid / tetrahydrofuran; water / 16 h / 60 °C

3: sodium hydride; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide; mineral oil / 16 h / -50 - 20 °C

With tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; In tetrahydrofuran; water; N,N-dimethyl-formamide; mineral oil;

DOI:10.1128/AAC.00722-13

upstream raw materials:

(6S)-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-ol

4-trifluoromethoxybenzyl bromide

(S)-1-((tert-butyldimethylsilyl)oxy)-3-(2-nitro-1H-imidazol-1-yl)propan-2-ol

1-((2S)-3-((tert-butyldimethylsilyl)oxy)-2-((tetrahydro-2H-pyran-2-yl)oxy)propyl)-2-nitro-1H-imidazole