(4S,5R)-(-)-3-(1'-oxo-2'(S)-fluoroisovaleryl)-4-methyl-5-phenyloxazolidin-2-one

Base Information

• Chemical Name: (4S,5R)-(-)-3-(1'-oxo-2'(S)-fluoroisovaleryl)-4-methyl-5-phenyloxazolidin-2-one
• CAS No.: 247039-00-5
• Molecular Formula: C₁₅H₁₈FNO₃
• Molecular Weight: 279.311

Synonyms:(4S,5R)-(-)-3-(1'-oxo-2'(S)-fluoroisovaleryl)-4-methyl-5-phenyloxazolidin-2-one

Chemical Property of (4S,5R)-(-)-3-(1'-oxo-2'(S)-fluoroisovaleryl)-4-methyl-5-phenyloxazolidin-2-one

Chemical Property:

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Technology Process of (4S,5R)-(-)-3-(1'-oxo-2'(S)-fluoroisovaleryl)-4-methyl-5-phenyloxazolidin-2-one

There total 3 articles about (4S,5R)-(-)-3-(1'-oxo-2'(S)-fluoroisovaleryl)-4-methyl-5-phenyloxazolidin-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: 76.0%

(4S,5R)-(-)-3-(1'-oxoisovaleryl)-4-methyl-5-phenyloxazolidin-2-one (247038-99-9) → (4S,5R)-(-)-3-(1'-oxo-2'(S)-fluoroisovaleryl)-4-methyl-5-phenyloxazolidin-2-one (247039-00-5)

Guidance literature:

With sodium hexamethyldisilazane; N-fluorobis(benzenesulfon)imide; In tetrahydrofuran; at -78 ℃; for 1h;

DOI:10.1021/jo990947n

Reference yield:

(4S,5R)-4-methyl-5-phenyl-oxazolidin-2-one (16251-45-9,17097-67-5,28044-22-6,28044-23-7,39663-75-7,54418-69-8,77943-39-6,125133-96-2,149055-02-7) → (4S,5R)-(-)-3-(1'-oxo-2'(S)-fluoroisovaleryl)-4-methyl-5-phenyloxazolidin-2-one (247039-00-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / n-BuLi / tetrahydrofuran / 3 h / -78 °C

2: 76 percent / NaHMDS; N-fluorobenzenesulfonimide / tetrahydrofuran / 1 h / -78 °C

With n-butyllithium; sodium hexamethyldisilazane; N-fluorobis(benzenesulfon)imide; In tetrahydrofuran; 1: Acylation / 2: Fluorination;

DOI:10.1021/jo990947n

Reference yield:

isopentanoyl chloride (108-12-3) → (4S,5R)-(-)-3-(1'-oxo-2'(S)-fluoroisovaleryl)-4-methyl-5-phenyloxazolidin-2-one (247039-00-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / n-BuLi / tetrahydrofuran / 3 h / -78 °C

2: 76 percent / NaHMDS; N-fluorobenzenesulfonimide / tetrahydrofuran / 1 h / -78 °C

With n-butyllithium; sodium hexamethyldisilazane; N-fluorobis(benzenesulfon)imide; In tetrahydrofuran; 1: Acylation / 2: Fluorination;

DOI:10.1021/jo990947n

upstream raw materials:

(4S,5R)-(-)-3-(1'-oxoisovaleryl)-4-methyl-5-phenyloxazolidin-2-one

(4S,5R)-4-methyl-5-phenyl-oxazolidin-2-one

isopentanoyl chloride

Downstream raw materials:

(R_S)-(+)-2-[N-(p-toluenesulfinamido)]-3-(S)-fluoroisohexanonitrile

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