(4R)-4-(phenyldifluoromethyl)-N-(2S,3R)-(3-hydroxy-2,4-dimethyl-pentanoyl)-1,3-oxazolidin-2-one

Base Information

• Chemical Name: (4R)-4-(phenyldifluoromethyl)-N-(2S,3R)-(3-hydroxy-2,4-dimethyl-pentanoyl)-1,3-oxazolidin-2-one
• CAS No.: 1020850-66-1
• Molecular Formula: C₁₇H₂₁F₂NO₄
• Molecular Weight: 341.355
• Mol file: 1020850-66-1.mol

Synonyms:(4R)-4-(phenyldifluoromethyl)-N-(2S,3R)-(3-hydroxy-2,4-dimethyl-pentanoyl)-1,3-oxazolidin-2-one

Chemical Property of (4R)-4-(phenyldifluoromethyl)-N-(2S,3R)-(3-hydroxy-2,4-dimethyl-pentanoyl)-1,3-oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R)-4-(phenyldifluoromethyl)-N-(2S,3R)-(3-hydroxy-2,4-dimethyl-pentanoyl)-1,3-oxazolidin-2-one

There total 10 articles about (4R)-4-(phenyldifluoromethyl)-N-(2S,3R)-(3-hydroxy-2,4-dimethyl-pentanoyl)-1,3-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: 89.0%

(-)-(4R)-4-(phenyldifluoromethyl)-3-propionyl-oxazolidin-2-one (1020850-60-5) + isobutyraldehyde (78-84-2) → (4R)-4-(phenyldifluoromethyl)-N-(2S,3R)-(3-hydroxy-2,4-dimethyl-pentanoyl)-1,3-oxazolidin-2-one (1020850-66-1) + (4R)-4-(phenyldifluoromethyl)-N-(2R,3S)-(3-hydroxy-2,4-dimethyl-pentanoyl)-1,3-oxazolidin-2-one (1020850-67-2)

Guidance literature:

(-)-(4R)-4-(phenyldifluoromethyl)-3-propionyl-oxazolidin-2-one; With titanium tetrachloride; (-)-sparteine; In dichloromethane; at 0 ℃; for 0.5h;

isobutyraldehyde; In dichloromethane; at -78 ℃; for 0.0833333h; Further stages.;

DOI:10.1016/j.jfluchem.2007.03.001

Reference yield: 77.0%

(-)-(4R)-4-(phenyldifluoromethyl)-3-propionyl-oxazolidin-2-one (1020850-60-5) + isobutyraldehyde (78-84-2) → (4R)-4-(phenyldifluoromethyl)-N-(2S,3R)-(3-hydroxy-2,4-dimethyl-pentanoyl)-1,3-oxazolidin-2-one (1020850-66-1) + (4R)-4-(phenyldifluoromethyl)-N-(2R,3S)-(3-hydroxy-2,4-dimethyl-pentanoyl)-1,3-oxazolidin-2-one (1020850-67-2) + (4R)-4-(phenyldifluoromethyl)-N-(2R*,3R*)-(3-hydroxy-2,4-dimethyl-pentanoyl)-1,3-oxazolidin-2-one

Guidance literature:

(-)-(4R)-4-(phenyldifluoromethyl)-3-propionyl-oxazolidin-2-one; With titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 0.5h;

isobutyraldehyde; In dichloromethane; at -78 ℃; Further stages.;

DOI:10.1016/j.jfluchem.2007.03.001

Reference yield:

(-)-(2S,Ss)-3,3-difluoro-3-phenyl-2-[N-(p-methoxyphenyl)]aminopropyl-(1-naphthyl)sulfoxide (1020850-63-8) → (4R)-4-(phenyldifluoromethyl)-N-(2S,3R)-(3-hydroxy-2,4-dimethyl-pentanoyl)-1,3-oxazolidin-2-one (1020850-66-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 78 percent / CAN; H₂O / acetonitrile / 20 °C

2.1: 92 percent / aq. K₂CO₃ / dioxane / 20 °C

3.1: TFAA; sym-collidine / acetonitrile / 0 °C

3.2: aq. K₂CO₃

3.3: 79 percent / NaBH₄ / H₂O

4.1: 91 percent / NaH / dimethylformamide / 0.5 h / 0 °C

5.1: NaH / dimethylformamide / 0.33 h / 0 °C

5.2: 87 percent / dimethylformamide / 1 h / 0 °C

6.1: TiCl₄; (-)-sparteine / CH₂Cl₂ / 0.5 h / 0 °C

6.2: 89 percent / CH₂Cl₂ / 0.08 h / -78 °C

With 2,4,6-trimethyl-pyridine; ammonium cerium(IV) nitrate; water; titanium tetrachloride; sodium hydride; potassium carbonate; trifluoroacetic anhydride; (-)-sparteine; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 3.1: Pummerer reaction;

DOI:10.1016/j.jfluchem.2007.03.001

upstream raw materials:

(-)-(4R)-4-(phenyldifluoromethyl)-3-propionyl-oxazolidin-2-one

isobutyraldehyde

(-)-(4R)-4-(phenyldifluoromethyl)-oxazolidin-2-one

(+)-(S_s)-{3,3-difluoro-3-phenyl-2-[N-(p-methoxyphenyl)imino]propyl}-(1-naphthyl)sulfoxide

Downstream raw materials:

(-)-(4R)-4-(phenyldifluoromethyl)-oxazolidin-2-one

(-)-(2S,3R)-3-hydroxy-2,4-dimethylpentanoic acid