(S)-tert-butyl 4-((S)-4-isopropyl-2-oxooxazolidin-3-yl)-4-oxo-3-phenylbutanoate

Base Information

• Chemical Name: (S)-tert-butyl 4-((S)-4-isopropyl-2-oxooxazolidin-3-yl)-4-oxo-3-phenylbutanoate
• CAS No.: 1378315-02-6
• Molecular Formula: C₂₀H₂₇NO₅
• Molecular Weight: 361.438

Synonyms:(S)-tert-butyl 4-((S)-4-isopropyl-2-oxooxazolidin-3-yl)-4-oxo-3-phenylbutanoate

Chemical Property of (S)-tert-butyl 4-((S)-4-isopropyl-2-oxooxazolidin-3-yl)-4-oxo-3-phenylbutanoate

Chemical Property:

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Technology Process of (S)-tert-butyl 4-((S)-4-isopropyl-2-oxooxazolidin-3-yl)-4-oxo-3-phenylbutanoate

There total 3 articles about (S)-tert-butyl 4-((S)-4-isopropyl-2-oxooxazolidin-3-yl)-4-oxo-3-phenylbutanoate 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: 50.0%

bromoacetic acid tert-butyl ester (5292-43-3) + (S)-4-iso-propyl-3-(2'-phenylacetyl)oxazolidin-2-one (103422-95-3,138690-03-6) → (S)-tert-butyl 4-((S)-4-isopropyl-2-oxooxazolidin-3-yl)-4-oxo-3-phenylbutanoate (1378315-02-6)

Guidance literature:

With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 - -50 ℃; for 2h; Inert atmosphere;

DOI:10.1021/ol300980k

Reference yield:

phenylacetic acid (103-82-2) → (S)-tert-butyl 4-((S)-4-isopropyl-2-oxooxazolidin-3-yl)-4-oxo-3-phenylbutanoate (1378315-02-6)

Guidance literature:

Multi-step reaction with 2 steps

1: pivaloyl chloride; triethylamine / toluene / 14 h / 80 - 110 °C / Inert atmosphere

2: sodium hexamethyldisilazane / tetrahydrofuran / 2 h / -78 - -50 °C / Inert atmosphere

With sodium hexamethyldisilazane; pivaloyl chloride; triethylamine; In tetrahydrofuran; toluene;

DOI:10.1021/ol300980k

Reference yield:

(4S)-4-isopropyl-1,3-oxazolidin-2-one (17016-83-0) → (S)-tert-butyl 4-((S)-4-isopropyl-2-oxooxazolidin-3-yl)-4-oxo-3-phenylbutanoate (1378315-02-6)

Guidance literature:

Multi-step reaction with 2 steps

1: pivaloyl chloride; triethylamine / toluene / 14 h / 80 - 110 °C / Inert atmosphere

2: sodium hexamethyldisilazane / tetrahydrofuran / 2 h / -78 - -50 °C / Inert atmosphere

With sodium hexamethyldisilazane; pivaloyl chloride; triethylamine; In tetrahydrofuran; toluene;

DOI:10.1021/ol300980k

upstream raw materials:

phenylacetic acid

bromoacetic acid tert-butyl ester

(S)-4-iso-propyl-3-(2'-phenylacetyl)oxazolidin-2-one

(4S)-4-isopropyl-1,3-oxazolidin-2-one

Downstream raw materials:

(S)-1-tert-butyl 4-(2,6-dimethylphenyl) 2-phenylsuccinate

(S)-4-tert-butyl 1-(2,6-dimethylphenyl) 2-phenylsuccinate

(S)-4-((S)-4-isopropyl-2-oxooxazolidin-3-yl)-4-oxo-3-phenylbutanoic acid

(S)-2,6-dimethylphenyl 4-((S)-4-isopropyl-2-oxooxazolidin-3-yl)-4-oxo-3-phenylbutanoate

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