(S)-4-Benzyl-3-[(S)-3-(3-benzyloxy-phenyl)-4,4-difluoro-butyryl]-oxazolidin-2-one

Base Information

• Chemical Name: (S)-4-Benzyl-3-[(S)-3-(3-benzyloxy-phenyl)-4,4-difluoro-butyryl]-oxazolidin-2-one
• CAS No.: 155697-48-6
• Molecular Formula: C₂₇H₂₅F₂NO₄
• Molecular Weight: 465.497
• Mol file: 155697-48-6.mol

Synonyms:

Chemical Property of (S)-4-Benzyl-3-[(S)-3-(3-benzyloxy-phenyl)-4,4-difluoro-butyryl]-oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-4-Benzyl-3-[(S)-3-(3-benzyloxy-phenyl)-4,4-difluoro-butyryl]-oxazolidin-2-one

There total 10 articles about (S)-4-Benzyl-3-[(S)-3-(3-benzyloxy-phenyl)-4,4-difluoro-butyryl]-oxazolidin-2-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:

3-Benzyloxybenzaldehyde (1700-37-4) → (S)-4-Benzyl-3-[(S)-3-(3-benzyloxy-phenyl)-4,4-difluoro-butyryl]-oxazolidin-2-one (155697-48-6)

Guidance literature:

Multi-step reaction with 10 steps

1: LiN(Si(CH₃)3)2 / tetrahydrofuran / 1 h / 0 deg C to RT

2: diisobutylaluminum hydride / toluene / 1 h / Ambient temperature

3: 85 percent / propionic acid / 2 h / 135 °C

4: diisobutylaluminum hydride / toluene / 1 h / Ambient temperature

5: DMAP, Et₃N / tetrahydrofuran / 1 h / Ambient temperature

6: O₃, Ph₃P / CH₂Cl₂; methanol / -70 deg C to RT

7: diethylaminosulfur trifluoride / CH₂Cl₂ / 1 h / Ambient temperature

8: K₂CO₃ / methanol / 1 h / Ambient temperature

9: pyridinium dichromate / dimethylformamide / 15 h / Ambient temperature

10: 1.) (CH₃)3CC(O)Cl, Et₃N / 1.) THF; 2.) THF

With dmap; dipyridinium dichromate; diethylamino-sulfur trifluoride; pivaloyl chloride; diisobutylaluminium hydride; potassium carbonate; ozone; triethylamine; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; propionic acid; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4039(00)73168-6

Reference yield:

(E)-3-(3-(benzyloxy)phenyl)prop-2-en-1-ol (155697-42-0) → (S)-4-Benzyl-3-[(S)-3-(3-benzyloxy-phenyl)-4,4-difluoro-butyryl]-oxazolidin-2-one (155697-48-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 85 percent / propionic acid / 2 h / 135 °C

2: diisobutylaluminum hydride / toluene / 1 h / Ambient temperature

3: DMAP, Et₃N / tetrahydrofuran / 1 h / Ambient temperature

4: O₃, Ph₃P / CH₂Cl₂; methanol / -70 deg C to RT

5: diethylaminosulfur trifluoride / CH₂Cl₂ / 1 h / Ambient temperature

6: K₂CO₃ / methanol / 1 h / Ambient temperature

7: pyridinium dichromate / dimethylformamide / 15 h / Ambient temperature

8: 1.) (CH₃)3CC(O)Cl, Et₃N / 1.) THF; 2.) THF

With dmap; dipyridinium dichromate; diethylamino-sulfur trifluoride; pivaloyl chloride; diisobutylaluminium hydride; potassium carbonate; ozone; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; propionic acid; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4039(00)73168-6

Reference yield:

3-(3-Benzyloxy-phenyl)-pent-4-en-1-ol → (S)-4-Benzyl-3-[(S)-3-(3-benzyloxy-phenyl)-4,4-difluoro-butyryl]-oxazolidin-2-one (155697-48-6)

Guidance literature:

Multi-step reaction with 6 steps

1: DMAP, Et₃N / tetrahydrofuran / 1 h / Ambient temperature

2: O₃, Ph₃P / CH₂Cl₂; methanol / -70 deg C to RT

3: diethylaminosulfur trifluoride / CH₂Cl₂ / 1 h / Ambient temperature

4: K₂CO₃ / methanol / 1 h / Ambient temperature

5: pyridinium dichromate / dimethylformamide / 15 h / Ambient temperature

6: 1.) (CH₃)3CC(O)Cl, Et₃N / 1.) THF; 2.) THF

With dmap; dipyridinium dichromate; diethylamino-sulfur trifluoride; pivaloyl chloride; potassium carbonate; ozone; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)73168-6

upstream raw materials:

(S)-4-benzyl-2-oxazolidinone lithium salt

3-difluoromethyl-3-(3-benzyloxyphenyl)propionic acid

3-Benzyloxybenzaldehyde

(E)-3-(3-(benzyloxy)phenyl)prop-2-en-1-ol

Downstream raw materials:

(S)-3-[(2S,3R)-2-Azido-3-(3-benzyloxy-phenyl)-4,4-difluoro-butyryl]-4-benzyl-oxazolidin-2-one