(4R)-4-benzyl-3-[(2S)-2-benzyloxymethyl-3-(2-fluoro-4-methoxyphenyl)propionyl]-2-oxazolidinone

Base Information

Chemical Name:(4R)-4-benzyl-3-[(2S)-2-benzyloxymethyl-3-(2-fluoro-4-methoxyphenyl)propionyl]-2-oxazolidinone
CAS No.:852181-21-6
Molecular Formula:C₂₈H₂₈FNO₅
Molecular Weight:477.532
Hs Code.:

Synonyms:(4R)-4-benzyl-3-[(2S)-2-benzyloxymethyl-3-(2-fluoro-4-methoxyphenyl)propionyl]-2-oxazolidinone

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Chemical Property of (4R)-4-benzyl-3-[(2S)-2-benzyloxymethyl-3-(2-fluoro-4-methoxyphenyl)propionyl]-2-oxazolidinone

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Technology Process of (4R)-4-benzyl-3-[(2S)-2-benzyloxymethyl-3-(2-fluoro-4-methoxyphenyl)propionyl]-2-oxazolidinone

There total 6 articles about (4R)-4-benzyl-3-[(2S)-2-benzyloxymethyl-3-(2-fluoro-4-methoxyphenyl)propionyl]-2-oxazolidinone 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: 81.0%

: 3587-60-8
Benzyloxymethyl chloride

: 852181-18-1
(4R)-4-benzyl-3-[3-(2-fluoro-4-methoxyphenyl)propionyl]-2-oxazolidinone

: 852181-21-6
(4R)-4-benzyl-3-[(2S)-2-benzyloxymethyl-3-(2-fluoro-4-methoxyphenyl)propionyl]-2-oxazolidinone

Guidance literature:: (4R)-4-benzyl-3-[3-(2-fluoro-4-methoxyphenyl)propionyl]-2-oxazolidinone; With titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 1h;

Benzyloxymethyl chloride; In dichloromethane; at 0 - 20 ℃; for 2h;
DOI:10.3390/90600449

Reference yield:

: 852181-14-7
3-(2-fluoro-4-methoxyphenyl)acrylic acid methyl ester

: 852181-21-6
(4R)-4-benzyl-3-[(2S)-2-benzyloxymethyl-3-(2-fluoro-4-methoxyphenyl)propionyl]-2-oxazolidinone

Guidance literature:: Multi-step reaction with 5 steps

1.1: H₂ / Pd/C / methanol / 20 h

2.1: 8.2 g / aq. NaOH / 3 h / Heating

3.1: SOCl₂ / dimethylformamide / 1 h / Heating

4.1: 5.06 g / n-BuLi; 1,10-phenanthroline / tetrahydrofuran; hexane / -78 °C

5.1: TiCl₄; diisopropylethylamine / CH₂Cl₂ / 1 h / 0 °C

5.2: 81 percent / CH₂Cl₂ / 2 h / 0 - 20 °C

With sodium hydroxide; n-butyllithium; thionyl chloride; 1,10-Phenanthroline; hydrogen; titanium tetrachloride; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.3390/90600449

Reference yield:

: 331-64-6
2-fluoro-4-methoxy-benzaldehyde

: 852181-21-6
(4R)-4-benzyl-3-[(2S)-2-benzyloxymethyl-3-(2-fluoro-4-methoxyphenyl)propionyl]-2-oxazolidinone

Guidance literature:: Multi-step reaction with 6 steps

1.1: NaH / dimethylformamide / 0.58 h / 0 - 20 °C

1.2: 75 percent / dimethylformamide / 20 h / 20 °C

2.1: H₂ / Pd/C / methanol / 20 h

3.1: 8.2 g / aq. NaOH / 3 h / Heating

4.1: SOCl₂ / dimethylformamide / 1 h / Heating

5.1: 5.06 g / n-BuLi; 1,10-phenanthroline / tetrahydrofuran; hexane / -78 °C

6.1: TiCl₄; diisopropylethylamine / CH₂Cl₂ / 1 h / 0 °C

6.2: 81 percent / CH₂Cl₂ / 2 h / 0 - 20 °C

With sodium hydroxide; n-butyllithium; thionyl chloride; 1,10-Phenanthroline; hydrogen; titanium tetrachloride; sodium hydride; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; 1.2: Horner-Emmons reaction;
DOI:10.3390/90600449