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

Base Information

• Chemical Name: (+)-(S_s)-{3,3-difluoro-3-phenyl-2-[N-(p-methoxyphenyl)imino]propyl}-(1-naphthyl)sulfoxide
• CAS No.: 1020850-62-7
• Molecular Formula: C₂₆H₂₁F₂NO₂S
• Molecular Weight: 449.521
• Mol file: 1020850-62-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

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

(S)-(-)-methyl 1-naphthyl sulfoxide (63699-45-6) + 2,2-difluoro-N-(4-methoxyphenyl)-2-phenylacetimidoyl chloride → (+)-(Ss)-{3,3-difluoro-3-phenyl-2-[N-(p-methoxyphenyl)imino]propyl}-(1-naphthyl)sulfoxide (1020850-62-7)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/j.jfluchem.2007.03.001

Reference yield: 91.0%

(+)-(Ss)-{3,3-difluoro-3-phenyl-2-[N-(p-methoxyphenyl)imino]propyl}-(1-naphthyl)sulfoxide (1020850-62-7) → (-)-(2S,Ss)-3,3-difluoro-3-phenyl-2-[N-(p-methoxyphenyl)]aminopropyl-(1-naphthyl)sulfoxide (1020850-63-8) + (2R,Ss)-3,3-difluoro-3-phenyl-2-[N-(p-methoxyphenyl)]aminopropyl-(1-naphthyl)sulfoxide

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; methanol; at -20 ℃; for 5h;

DOI:10.1016/j.jfluchem.2007.03.001

Reference yield:

(+)-(Ss)-{3,3-difluoro-3-phenyl-2-[N-(p-methoxyphenyl)imino]propyl}-(1-naphthyl)sulfoxide (1020850-62-7) → (4R)-4-(phenyldifluoromethyl)-N-(2R,3S)-(3-hydroxy-2,4-dimethyl-pentanoyl)-1,3-oxazolidin-2-one (1020850-67-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 91 percent / NaBH₄ / tetrahydrofuran; methanol / 5 h / -20 °C

2.1: 78 percent / CAN; H₂O / acetonitrile / 20 °C

3.1: 92 percent / aq. K₂CO₃ / dioxane / 20 °C

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

4.2: aq. K₂CO₃

4.3: 79 percent / NaBH₄ / H₂O

5.1: 91 percent / NaH / dimethylformamide / 0.5 h / 0 °C

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

6.2: 87 percent / dimethylformamide / 1 h / 0 °C

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

7.2: CH₂Cl₂ / 0.08 h / -78 °C

With 2,4,6-trimethyl-pyridine; sodium tetrahydroborate; ammonium cerium(IV) nitrate; water; titanium tetrachloride; sodium hydride; potassium carbonate; trifluoroacetic anhydride; (-)-sparteine; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 4.1: Pummerer reaction;

DOI:10.1016/j.jfluchem.2007.03.001

upstream raw materials:

(S)-(-)-methyl 1-naphthyl sulfoxide

Downstream raw materials:

(-)-(2S,S_s)-3,3-difluoro-3-phenyl-2-[N-(p-methoxyphenyl)]aminopropyl-(1-naphthyl)sulfoxide

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

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

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