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

Base Information

• Chemical Name: {(S)-3-[2-((S)-3-Acetyl-2-oxo-oxazolidin-4-yl)-acetyl]-2-oxo-oxazolidin-4-yl}-acetic acid pentafluorophenyl ester
• CAS No.: 760979-70-2
• Molecular Formula: C₁₈H₁₃F₅N₂O₈
• Molecular Weight: 480.302

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of {(S)-3-[2-((S)-3-Acetyl-2-oxo-oxazolidin-4-yl)-acetyl]-2-oxo-oxazolidin-4-yl}-acetic acid pentafluorophenyl ester

There total 6 articles about {(S)-3-[2-((S)-3-Acetyl-2-oxo-oxazolidin-4-yl)-acetyl]-2-oxo-oxazolidin-4-yl}-acetic acid pentafluorophenyl 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: 95.0%

pentafluorophenyl trifloroacetate (14533-84-7) + {(S)-3-[2-((S)-3-Acetyl-2-oxo-oxazolidin-4-yl)-acetyl]-2-oxo-oxazolidin-4-yl}-acetic acid (760979-69-9) → {(S)-3-[2-((S)-3-Acetyl-2-oxo-oxazolidin-4-yl)-acetyl]-2-oxo-oxazolidin-4-yl}-acetic acid pentafluorophenyl ester (760979-70-2)

Guidance literature:

With pyridine; In N,N-dimethyl-formamide; at 20 ℃; for 0.75h;

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 pentafluorophenyl ester (760979-70-2)

Guidance literature:

Multi-step reaction with 9 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

8.1: 92 percent / H₂ / Pd/C / ethyl acetate / 1 h / 20 °C / 2280 Torr

9.1: 95 percent / pyridine / dimethylformamide / 0.75 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 pentafluorophenyl ester (760979-70-2)

Guidance literature:

Multi-step reaction with 7 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

6.1: 92 percent / H₂ / Pd/C / ethyl acetate / 1 h / 20 °C / 2280 Torr

7.1: 95 percent / pyridine / dimethylformamide / 0.75 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:

pentafluorophenyl trifloroacetate

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

N-Cbz-L-Asp

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

Downstream raw materials:

[(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-[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 benzyl ester

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