(R)-3-[(R)-8-Chloro-3-(2-fluoro-phenyl)-5,6-dihydro-furo[2',3':4,5]benzo[1,2-d]isoxazole-6-carbonyl]-4-phenyl-oxazolidin-2-one

Base Information

• Chemical Name: (R)-3-[(R)-8-Chloro-3-(2-fluoro-phenyl)-5,6-dihydro-furo[2',3':4,5]benzo[1,2-d]isoxazole-6-carbonyl]-4-phenyl-oxazolidin-2-one
• CAS No.: 90247-26-0
• Molecular Formula: C₂₅H₁₆ClFN₂O₅
• Molecular Weight: 478.864
• Mol file: 90247-26-0.mol

Synonyms:(R)-3-[(R)-8-Chloro-3-(2-fluoro-phenyl)-5,6-dihydro-furo[2',3':4,5]benzo[1,2-d]isoxazole-6-carbonyl]-4-phenyl-oxazolidin-2-one

Chemical Property of (R)-3-[(R)-8-Chloro-3-(2-fluoro-phenyl)-5,6-dihydro-furo[2',3':4,5]benzo[1,2-d]isoxazole-6-carbonyl]-4-phenyl-oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-3-[(R)-8-Chloro-3-(2-fluoro-phenyl)-5,6-dihydro-furo[2',3':4,5]benzo[1,2-d]isoxazole-6-carbonyl]-4-phenyl-oxazolidin-2-one

There total 14 articles about (R)-3-[(R)-8-Chloro-3-(2-fluoro-phenyl)-5,6-dihydro-furo[2',3':4,5]benzo[1,2-d]isoxazole-6-carbonyl]-4-phenyl-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:

2-chlororesorcinol dimethyl ether (7051-15-2) → (R)-3-[(R)-8-Chloro-3-(2-fluoro-phenyl)-5,6-dihydro-furo[2',3':4,5]benzo[1,2-d]isoxazole-6-carbonyl]-4-phenyl-oxazolidin-2-one (90247-26-0)

Guidance literature:

Multi-step reaction with 13 steps

1: 79 percent / TiCl₄ / CH₂Cl₂ / 1 h / 0 °C

2: 74 percent / BBr₃ / CH₂Cl₂ / 1 h / 0 °C

3: 79.6 percent / K₂CO₃ / butan-2-one / 4.5 h / Heating

4: 82.9 percent / H₂, conc.H₂SO₄ / 20percent Pd/C / acetic acid / 2 h / 2280 Torr

5: LiCl, Me₂SO, H₂O / 2 h / Heating

6: H₂SO₄ / Ambient temperature

7: 69.2 percent / AlCl₃ / 1,2-dichloro-ethane / 3.75 h / 5 - 20 °C

8: 20 percent / NH₂OH*HCl, pyridine / 4 h / Heating

9: 58 percent / 1 h / 90 °C

10: NaH / dimethylformamide / 4 h / Ambient temperature

11: 92 percent / aq. KOH / methanol / 1 h

12: SOCl₂ / benzene / 2 h / Heating

13: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 1.5 h, 2.) THF, hexane, from -78 to -30 deg C, 1.6 h

With pyridine; potassium hydroxide; n-butyllithium; aluminium trichloride; thionyl chloride; sulfuric acid; hydroxylamine hydrochloride; water; hydrogen; boron tribromide; titanium tetrachloride; sodium hydride; potassium carbonate; dimethyl sulfoxide; lithium chloride; palladium on activated charcoal; In methanol; dichloromethane; acetic acid; 1,2-dichloro-ethane; N,N-dimethyl-formamide; butanone; benzene;

DOI:10.1021/jm00374a014

Reference yield:

3-chloro-2,4-dimethoxybenzaldehyde (72482-14-5) → (R)-3-[(R)-8-Chloro-3-(2-fluoro-phenyl)-5,6-dihydro-furo[2',3':4,5]benzo[1,2-d]isoxazole-6-carbonyl]-4-phenyl-oxazolidin-2-one (90247-26-0)

Guidance literature:

Multi-step reaction with 12 steps

1: 74 percent / BBr₃ / CH₂Cl₂ / 1 h / 0 °C

2: 79.6 percent / K₂CO₃ / butan-2-one / 4.5 h / Heating

3: 82.9 percent / H₂, conc.H₂SO₄ / 20percent Pd/C / acetic acid / 2 h / 2280 Torr

4: LiCl, Me₂SO, H₂O / 2 h / Heating

5: H₂SO₄ / Ambient temperature

6: 69.2 percent / AlCl₃ / 1,2-dichloro-ethane / 3.75 h / 5 - 20 °C

7: 20 percent / NH₂OH*HCl, pyridine / 4 h / Heating

8: 58 percent / 1 h / 90 °C

9: NaH / dimethylformamide / 4 h / Ambient temperature

10: 92 percent / aq. KOH / methanol / 1 h

11: SOCl₂ / benzene / 2 h / Heating

12: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 1.5 h, 2.) THF, hexane, from -78 to -30 deg C, 1.6 h

With pyridine; potassium hydroxide; n-butyllithium; aluminium trichloride; thionyl chloride; sulfuric acid; hydroxylamine hydrochloride; water; hydrogen; boron tribromide; sodium hydride; potassium carbonate; dimethyl sulfoxide; lithium chloride; palladium on activated charcoal; In methanol; dichloromethane; acetic acid; 1,2-dichloro-ethane; N,N-dimethyl-formamide; butanone; benzene;

DOI:10.1021/jm00374a014

Reference yield:

3-chloro-2-hydroxy-4-methoxybenzaldehyde (72482-15-6) → (R)-3-[(R)-8-Chloro-3-(2-fluoro-phenyl)-5,6-dihydro-furo[2',3':4,5]benzo[1,2-d]isoxazole-6-carbonyl]-4-phenyl-oxazolidin-2-one (90247-26-0)

Guidance literature:

Multi-step reaction with 11 steps

1: 79.6 percent / K₂CO₃ / butan-2-one / 4.5 h / Heating

2: 82.9 percent / H₂, conc.H₂SO₄ / 20percent Pd/C / acetic acid / 2 h / 2280 Torr

3: LiCl, Me₂SO, H₂O / 2 h / Heating

4: H₂SO₄ / Ambient temperature

5: 69.2 percent / AlCl₃ / 1,2-dichloro-ethane / 3.75 h / 5 - 20 °C

6: 20 percent / NH₂OH*HCl, pyridine / 4 h / Heating

7: 58 percent / 1 h / 90 °C

8: NaH / dimethylformamide / 4 h / Ambient temperature

9: 92 percent / aq. KOH / methanol / 1 h

10: SOCl₂ / benzene / 2 h / Heating

11: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 1.5 h, 2.) THF, hexane, from -78 to -30 deg C, 1.6 h

With pyridine; potassium hydroxide; n-butyllithium; aluminium trichloride; thionyl chloride; sulfuric acid; hydroxylamine hydrochloride; water; hydrogen; sodium hydride; potassium carbonate; dimethyl sulfoxide; lithium chloride; palladium on activated charcoal; In methanol; acetic acid; 1,2-dichloro-ethane; N,N-dimethyl-formamide; butanone; benzene;

DOI:10.1021/jm00374a014

upstream raw materials:

(4R)-phenyl-2-oxazolidinone

8-chloro-5,6-dihydro-3-(o-fluorophenyl)furo<3,2-f>-1,2-benzisoxazole-6-carbonyl chloride

2-chlororesorcinol dimethyl ether

D-2-phenylglycinol

Downstream raw materials:

(R)-8-Chloro-3-(2-fluoro-phenyl)-5,6-dihydro-furo[2',3':4,5]benzo[1,2-d]isoxazole-6-carboxylic acid

Refernces