(5S)-5-[2-(benzyloxycarbonylamino)ethyl]-2,2-bis(trifluoromethyl)-5-methyl-1,3-dioxolan-4-one

Base Information

• Chemical Name: (5S)-5-[2-(benzyloxycarbonylamino)ethyl]-2,2-bis(trifluoromethyl)-5-methyl-1,3-dioxolan-4-one
• CAS No.: 637777-04-9
• Molecular Formula: C₁₆H₁₅F₆NO₅
• Molecular Weight: 415.289
• Mol file: 637777-04-9.mol

Synonyms:(5S)-5-[2-(benzyloxycarbonylamino)ethyl]-2,2-bis(trifluoromethyl)-5-methyl-1,3-dioxolan-4-one

Chemical Property of (5S)-5-[2-(benzyloxycarbonylamino)ethyl]-2,2-bis(trifluoromethyl)-5-methyl-1,3-dioxolan-4-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S)-5-[2-(benzyloxycarbonylamino)ethyl]-2,2-bis(trifluoromethyl)-5-methyl-1,3-dioxolan-4-one

There total 6 articles about (5S)-5-[2-(benzyloxycarbonylamino)ethyl]-2,2-bis(trifluoromethyl)-5-methyl-1,3-dioxolan-4-one 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: 74.0%

benzyl alcohol (100-51-6,185532-71-2) + (5S)-5-(2-isocyanatoethyl)-5-methyl-2,2-bis(trifluoromethyl)-1,3-dioxolan-4-one (637777-02-7) → (5S)-5-[2-(benzyloxycarbonylamino)ethyl]-2,2-bis(trifluoromethyl)-5-methyl-1,3-dioxolan-4-one (637777-04-9)

Guidance literature:

In chloroform; for 12h; Heating;

DOI:10.1055/s-2003-41477

Reference yield:

[(5S)-2,2-Bis(trifluoromethyl)-5-methyl-4-oxo-1,3-dioxolan-5-yl] acetic acid (184305-30-4) → (5S)-5-[2-(benzyloxycarbonylamino)ethyl]-2,2-bis(trifluoromethyl)-5-methyl-1,3-dioxolan-4-one (637777-04-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 86 percent / SOCl₂ / Heating

2: 90 percent / diethyl ether / -78 - 0 °C

3: 77 percent / silver benzoate / Heating

4: 78 percent / SOCl₂ / 12 h / Heating

5: 70 percent / trimethylsilyl azide / toluene / 20 - 90 °C

6: 74 percent / CHCl₃ / 12 h / Heating

With thionyl chloride; trimethylsilylazide; silver benzoate; In diethyl ether; chloroform; toluene; 2: Arndt-Eistert reaction / 3: Wolff rearrangement / 5: Curtius rearrangement;

DOI:10.1007/s00706-005-0291-1

Reference yield:

[(5S)-2,2-Bis(trifluoromethyl)-5-methyl-4-oxo-1,3-dioxolan-5-yl] acetyl chloride (184305-31-5) → (5S)-5-[2-(benzyloxycarbonylamino)ethyl]-2,2-bis(trifluoromethyl)-5-methyl-1,3-dioxolan-4-one (637777-04-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / diethyl ether / -78 - 0 °C

2: 77 percent / silver benzoate / Heating

3: 78 percent / SOCl₂ / 12 h / Heating

4: 70 percent / trimethylsilyl azide / toluene / 20 - 90 °C

5: 74 percent / CHCl₃ / 12 h / Heating

With thionyl chloride; trimethylsilylazide; silver benzoate; In diethyl ether; chloroform; toluene; 1: Arndt-Eistert reaction / 2: Wolff rearrangement / 4: Curtius rearrangement;

DOI:10.1007/s00706-005-0291-1

upstream raw materials:

benzyl alcohol

(5S)-5-(2-isocyanatoethyl)-5-methyl-2,2-bis(trifluoromethyl)-1,3-dioxolan-4-one

[(5S)-2,2-Bis(trifluoromethyl)-5-methyl-4-oxo-1,3-dioxolan-5-yl] acetic acid

[(5S)-2,2-Bis(trifluoromethyl)-5-methyl-4-oxo-1,3-dioxolan-5-yl] acetyl chloride