{(S)-3-[2-((S)-3-Acetyl-2-oxo-oxazolidin-4-yl)-acetyl]-2-oxo-oxazolidin-4-yl}-acetic acid benzyl ester

Base Information

• Chemical Name: {(S)-3-[2-((S)-3-Acetyl-2-oxo-oxazolidin-4-yl)-acetyl]-2-oxo-oxazolidin-4-yl}-acetic acid benzyl ester
• CAS No.: 760979-68-8
• Molecular Formula: C₁₉H₂₀N₂O₈
• Molecular Weight: 404.376
• Mol file: 760979-68-8.mol

Synonyms:{(S)-3-[2-((S)-3-Acetyl-2-oxo-oxazolidin-4-yl)-acetyl]-2-oxo-oxazolidin-4-yl}-acetic acid benzyl ester

Chemical Property of {(S)-3-[2-((S)-3-Acetyl-2-oxo-oxazolidin-4-yl)-acetyl]-2-oxo-oxazolidin-4-yl}-acetic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(S)-3-[2-((S)-3-Acetyl-2-oxo-oxazolidin-4-yl)-acetyl]-2-oxo-oxazolidin-4-yl}-acetic acid benzyl ester

There total 7 articles about {(S)-3-[2-((S)-3-Acetyl-2-oxo-oxazolidin-4-yl)-acetyl]-2-oxo-oxazolidin-4-yl}-acetic acid benzyl ester 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: 70.0%

(S)-(2-oxo)oxazolidine-4-acetic acid benzyl ester (540496-34-2) + ((S)-3-Acetyl-2-oxo-oxazolidin-4-yl)-acetic acid pentafluorophenyl ester (760979-67-7) → {(S)-3-[2-((S)-3-Acetyl-2-oxo-oxazolidin-4-yl)-acetyl]-2-oxo-oxazolidin-4-yl}-acetic acid benzyl ester (760979-68-8)

Guidance literature:

With dmap; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 16h;

DOI:10.1039/b405856a

Reference yield:

N-Cbz-L-Asp (1152-61-0) → {(S)-3-[2-((S)-3-Acetyl-2-oxo-oxazolidin-4-yl)-acetyl]-2-oxo-oxazolidin-4-yl}-acetic acid benzyl ester (760979-68-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 95 percent / Ac₂O / 0.02 h / microwave irradiation

2.1: 80 percent / NaBH₄ / tetrahydrofuran / 16 h / 20 °C

3.1: aq. Cs₂CO₃ / acetone / 3 h / Heating

3.2: 60 percent / dimethylformamide / 24 h / 20 °C

4.1: 95 percent / DIEA; DMAP / dimethylformamide / 24 h / 20 °C

5.1: 100 percent / H₂ / Pd/C / ethyl acetate / 1 h / 20 °C / 2280 Torr

6.1: 100 percent / pyridine / dimethylformamide / 0.75 h / 20 °C

7.1: 70 percent / DIEA; DMAP / dimethylformamide / 16 h / 20 °C

With pyridine; dmap; sodium tetrahydroborate; hydrogen; acetic anhydride; caesium carbonate; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide; acetone;

DOI:10.1039/b405856a

Reference yield:

benzyl (3S)-5-oxotetrahydro-3-furanylcarbamate (87219-29-2) → {(S)-3-[2-((S)-3-Acetyl-2-oxo-oxazolidin-4-yl)-acetyl]-2-oxo-oxazolidin-4-yl}-acetic acid benzyl ester (760979-68-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: aq. Cs₂CO₃ / acetone / 3 h / Heating

1.2: 60 percent / dimethylformamide / 24 h / 20 °C

2.1: 95 percent / DIEA; DMAP / dimethylformamide / 24 h / 20 °C

3.1: 100 percent / H₂ / Pd/C / ethyl acetate / 1 h / 20 °C / 2280 Torr

4.1: 100 percent / pyridine / dimethylformamide / 0.75 h / 20 °C

5.1: 70 percent / DIEA; DMAP / dimethylformamide / 16 h / 20 °C

With pyridine; dmap; hydrogen; caesium carbonate; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In ethyl acetate; N,N-dimethyl-formamide; acetone;

DOI:10.1039/b405856a

upstream raw materials:

(S)-(2-oxo)oxazolidine-4-acetic acid benzyl ester

((S)-3-Acetyl-2-oxo-oxazolidin-4-yl)-acetic acid pentafluorophenyl ester

N-Cbz-L-Asp

benzyl (3S)-5-oxotetrahydro-3-furanylcarbamate

Downstream raw materials:

((S)-3-{2-[(S)-3-(2-{(S)-3-[2-((S)-3-Acetyl-2-oxo-oxazolidin-4-yl)-acetyl]-2-oxo-oxazolidin-4-yl}-acetyl)-2-oxo-oxazolidin-4-yl]-acetyl}-2-oxo-oxazolidin-4-yl)-acetic acid benzyl ester

[(S)-3-(2-{(S)-3-[2-((S)-3-Acetyl-2-oxo-oxazolidin-4-yl)-acetyl]-2-oxo-oxazolidin-4-yl}-acetyl)-2-oxo-oxazolidin-4-yl]-acetic acid pentafluorophenyl ester

[(S)-3-(2-{(S)-3-[2-((S)-3-Acetyl-2-oxo-oxazolidin-4-yl)-acetyl]-2-oxo-oxazolidin-4-yl}-acetyl)-2-oxo-oxazolidin-4-yl]-acetic acid benzyl ester