(S)-4-(4-(benzyloxy)benzyl)-3-acetyloxazolidin-2-one

Base Information

• Chemical Name: (S)-4-(4-(benzyloxy)benzyl)-3-acetyloxazolidin-2-one
• CAS No.: 931527-16-1
• Molecular Formula: C₁₉H₁₉NO₄
• Molecular Weight: 325.364
• Mol file: 931527-16-1.mol

Synonyms:(S)-4-(4-(benzyloxy)benzyl)-3-acetyloxazolidin-2-one

Chemical Property of (S)-4-(4-(benzyloxy)benzyl)-3-acetyloxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-4-(4-(benzyloxy)benzyl)-3-acetyloxazolidin-2-one

There total 1 articles about (S)-4-(4-(benzyloxy)benzyl)-3-acetyloxazolidin-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: 95.0%

acetic anhydride (108-24-7) + O-benzyl N-Boc-L-tyrosinol (66605-58-1) → (S)-4-(4-(benzyloxy)benzyl)-3-acetyloxazolidin-2-one (931527-16-1)

Guidance literature:

O-benzyl N-Boc-L-tyrosinol; With sodium hydride; In tetrahydrofuran; at 20 ℃; for 3h;

acetic anhydride; In tetrahydrofuran; at 20 ℃; for 1h; Further stages.;

DOI:10.1016/j.tetlet.2007.01.006

Reference yield: 100.0%

(S)-4-(4-(benzyloxy)benzyl)-3-acetyloxazolidin-2-one (931527-16-1) → (S)-4-(4-hydroxybenzyl)-3-acetyloxazolidin-2-one (931527-23-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; ethyl acetate; at 20 ℃; for 2h;

DOI:10.1016/j.tetlet.2007.01.006

Reference yield:

(S)-4-(4-(benzyloxy)benzyl)-3-acetyloxazolidin-2-one (931527-16-1) → C26H24F3NO4

Guidance literature:

Multi-step reaction with 12 steps

1.1: 100 percent / hydrogen / Pd/C / ethanol; ethyl acetate / 2 h / 20 °C

2.1: 83 percent / [bis(trifluoroacetoxy)iodo]benzene / acetonitrile; H₂O / 0.5 h / 20 °C

3.1: 95 percent / pyridine / 60 h / 20 °C

4.1: sulfuric acid / 0.42 h / 20 °C

4.2: 82 percent / aq. K₂CO₃ / 1 h

5.1: soodium methoxide / methanol / 2 h / 20 °C

6.1: pyridine / 4 h / 20 °C

7.1: 110.3 mg / DMAP / tetrahydrofuran / 2 h / 20 °C

8.1: K₂CO₃; methanol / tetrahydrofuran

9.1: 83 percent / NaH / tetrahydrofuran / 60 °C

10.1: K₂CO₃ / acetonitrile

11.1: TFA / CH₂Cl₂

12.1: EDC; HOBT; (i-Pr)2EtN / CH₂Cl₂; dimethylformamide

With pyridine; methanol; dmap; sulfuric acid; hydrogen; sodium hydride; potassium carbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; bis-[(trifluoroacetoxy)iodo]benzene; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.tetlet.2007.01.006

upstream raw materials:

acetic anhydride

O-benzyl N-Boc-L-tyrosinol

Downstream raw materials:

(S)-4-(4-hydroxybenzyl)-3-acetyloxazolidin-2-one

(S)-3-acetyl-4-((1-hydroxy-4-oxocyclohexa-2,5-dienyl)methyl)oxazolidin-2-one

(S)-3-acetyl-4-((1-acetoxy-4-oxocyclohexa-2,5-dienyl)methyl)oxazolidin-2-one

(S)-4-(2,4-diacetoxybenzyl)-3-acetyloxazolidin-2-one