(4S)-3-((2S)-4-(tert-butoxy)-2-(1,1-dimethylethyl)-4-oxobutanoyl)-4-(phenylmethyl)-1,3-oxazolidin-2-one

Base Information

• Chemical Name: (4S)-3-((2S)-4-(tert-butoxy)-2-(1,1-dimethylethyl)-4-oxobutanoyl)-4-(phenylmethyl)-1,3-oxazolidin-2-one
• CAS No.: 245323-37-9
• Molecular Formula: C₂₂H₃₁NO₅
• Molecular Weight: 389.492
• Mol file: 245323-37-9.mol

Synonyms:(4S)-3-((2S)-4-(tert-butoxy)-2-(1,1-dimethylethyl)-4-oxobutanoyl)-4-(phenylmethyl)-1,3-oxazolidin-2-one

Chemical Property of (4S)-3-((2S)-4-(tert-butoxy)-2-(1,1-dimethylethyl)-4-oxobutanoyl)-4-(phenylmethyl)-1,3-oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S)-3-((2S)-4-(tert-butoxy)-2-(1,1-dimethylethyl)-4-oxobutanoyl)-4-(phenylmethyl)-1,3-oxazolidin-2-one

There total 1 articles about (4S)-3-((2S)-4-(tert-butoxy)-2-(1,1-dimethylethyl)-4-oxobutanoyl)-4-(phenylmethyl)-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: 82.0%

bromoacetic acid tert-butyl ester (5292-43-3) + (S)-4-benzyl-3-(3,3-dimethylbutanoyl)oxazolidin-2-one (104266-91-3) → (4S)-3-((2S)-4-(tert-butoxy)-2-(1,1-dimethylethyl)-4-oxobutanoyl)-4-(phenylmethyl)-1,3-oxazolidin-2-one (245323-37-9)

Guidance literature:

With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 15h;

DOI:10.1021/jo990756k

Reference yield:

(4S)-3-((2S)-4-(tert-butoxy)-2-(1,1-dimethylethyl)-4-oxobutanoyl)-4-(phenylmethyl)-1,3-oxazolidin-2-one (245323-37-9) → tert-butyl (3S)-N-(benzyloxycarbonyl)-3-amino-4,4-dimethylpentanoate

Guidance literature:

Multi-step reaction with 3 steps

1.1: 85 percent / n-BuLi / hexane; tetrahydrofuran / -78 - 0 °C

2.1: 100 percent / H₂O₂; LiOH*H₂O / tetrahydrofuran; H₂O / 72 h / 20 °C

3.1: Et₃N; EtCO₂Cl; NaN₃ / toluene; H₂O / 0 - 25 °C

3.2: 74 percent / toluene / 12 h / Heating

With lithium hydroxide; n-butyllithium; sodium azide; dihydrogen peroxide; propionyl chloride; triethylamine; In tetrahydrofuran; hexane; water; toluene; 1.1: Hydrolysis / 2.1: Hydrolysis / 3.1: Rearrangement / 3.2: Rearrangement;

DOI:10.1021/jo990756k

Reference yield:

(4S)-3-((2S)-4-(tert-butoxy)-2-(1,1-dimethylethyl)-4-oxobutanoyl)-4-(phenylmethyl)-1,3-oxazolidin-2-one (245323-37-9) → (S)-4-(tert-butoxy)-2-(1,1-dimethylethyl)-4-oxobutanoic acid (210048-06-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / n-BuLi / hexane; tetrahydrofuran / -78 - 0 °C

2: 100 percent / H₂O₂; LiOH*H₂O / tetrahydrofuran; H₂O / 72 h / 20 °C

With lithium hydroxide; n-butyllithium; dihydrogen peroxide; In tetrahydrofuran; hexane; water; 1: Hydrolysis / 2: Hydrolysis;

DOI:10.1021/jo990756k

upstream raw materials:

bromoacetic acid tert-butyl ester

(S)-4-benzyl-3-(3,3-dimethylbutanoyl)oxazolidin-2-one

Downstream raw materials:

(S)-4-(tert-butoxy)-2-(1,1-dimethylethyl)-4-oxobutanoic acid