4-{4-[Benzyloxycarbonyl-((S)-2,3-dihydroxy-propyl)-amino]-2-fluoro-phenyl}-piperazine-1-carboxylic acid benzyl ester

Base Information

• Chemical Name: 4-{4-[Benzyloxycarbonyl-((S)-2,3-dihydroxy-propyl)-amino]-2-fluoro-phenyl}-piperazine-1-carboxylic acid benzyl ester
• CAS No.: 912552-59-1
• Molecular Formula: C₂₉H₃₂FN₃O₆
• Molecular Weight: 537.588

Synonyms:4-{4-[Benzyloxycarbonyl-((S)-2,3-dihydroxy-propyl)-amino]-2-fluoro-phenyl}-piperazine-1-carboxylic acid benzyl ester

Chemical Property of 4-{4-[Benzyloxycarbonyl-((S)-2,3-dihydroxy-propyl)-amino]-2-fluoro-phenyl}-piperazine-1-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of 4-{4-[Benzyloxycarbonyl-((S)-2,3-dihydroxy-propyl)-amino]-2-fluoro-phenyl}-piperazine-1-carboxylic acid benzyl ester

There total 8 articles about 4-{4-[Benzyloxycarbonyl-((S)-2,3-dihydroxy-propyl)-amino]-2-fluoro-phenyl}-piperazine-1-carboxylic 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: 82.0%

4-{4-[benzyloxycarbonyl-(3-oxo-propyl)-amino]-2-fluoro-phenyl}-piperazine-1-carboxylic acid benzyl ester (912552-58-0) → 4-{4-[Benzyloxycarbonyl-((S)-2,3-dihydroxy-propyl)-amino]-2-fluoro-phenyl}-piperazine-1-carboxylic acid benzyl ester (912552-59-1)

Guidance literature:

4-{4-[benzyloxycarbonyl-(3-oxo-propyl)-amino]-2-fluoro-phenyl}-piperazine-1-carboxylic acid benzyl ester; With Nitrosobenzene; D-Prolin; In acetonitrile; at -20 ℃; for 24h;

With sodium tetrahydroborate; In methanol;

With copper(II) sulfate; In methanol;

DOI:10.1016/j.tetlet.2006.07.065

Reference yield:

(S)-N-[[3-[3-fluoro-4-(1-piperazinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide (154590-66-6,154590-43-9) → 4-{4-[Benzyloxycarbonyl-((S)-2,3-dihydroxy-propyl)-amino]-2-fluoro-phenyl}-piperazine-1-carboxylic acid benzyl ester (912552-59-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 100 percent / Et₃N / CH₂Cl₂ / 0 °C

2.1: 89 percent / H₂ / Pd/C / methanol; CH₂Cl₂ / 760 Torr

3.1: NaI; Na₂CO₃ / dimethylformamide / 65 °C

4.1: aq. NaHCO₃ / acetone

5.1: 94 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - -60 °C

6.1: nitrosobenzene; D-proline / acetonitrile / 24 h / -20 °C

6.2: NaBH₄ / methanol

6.3: 82 percent / CuSO₄ / methanol

With oxalyl dichloride; hydrogen; sodium hydrogencarbonate; sodium carbonate; dimethyl sulfoxide; triethylamine; Nitrosobenzene; D-Prolin; sodium iodide; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile; 5.1: Swern oxidation;

DOI:10.1016/j.tetlet.2006.07.065

Reference yield:

N-((S)-3-{4-[4-(2-Benzyloxy-acetyl)-piperazin-1-yl]-3-fluoro-phenyl}-2-oxo-oxazolidin-5-ylmethyl)-acetamide (174649-08-2) → 4-{4-[Benzyloxycarbonyl-((S)-2,3-dihydroxy-propyl)-amino]-2-fluoro-phenyl}-piperazine-1-carboxylic acid benzyl ester (912552-59-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 89 percent / H₂ / Pd/C / methanol; CH₂Cl₂ / 760 Torr

2.1: NaI; Na₂CO₃ / dimethylformamide / 65 °C

3.1: aq. NaHCO₃ / acetone

4.1: 94 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - -60 °C

5.1: nitrosobenzene; D-proline / acetonitrile / 24 h / -20 °C

5.2: NaBH₄ / methanol

5.3: 82 percent / CuSO₄ / methanol

With oxalyl dichloride; hydrogen; sodium hydrogencarbonate; sodium carbonate; dimethyl sulfoxide; triethylamine; Nitrosobenzene; D-Prolin; sodium iodide; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile; 4.1: Swern oxidation;

DOI:10.1016/j.tetlet.2006.07.065

upstream raw materials:

4-{4-[benzyloxycarbonyl-(3-oxo-propyl)-amino]-2-fluoro-phenyl}-piperazine-1-carboxylic acid benzyl ester

4-{4-[benzyloxycarbonyl-(3-hydroxy-propyl)-amino]-2-fluoro-phenyl}-piperazine-1-carboxylic acid benzyl ester

benzyl chloroformate

(S)-N-[[3-[3-fluoro-4-(1-piperazinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

Downstream raw materials:

(R)-[N-3-[3-fluoro-4-[N-1-(4-carbobenzoxy)piperazinyl]-phenyl]-2-oxo-5-oxazolidinyl]methyl azide

4-[2-Fluoro-4-((R)-5-methanesulfonyloxymethyl-2-oxo-oxazolidin-3-yl)-phenyl]-piperazine-1-carboxylic acid benzyl ester

(S)-N-(3-(3-fluoro-4-((N-4-carbobenzoxy)piperazin-1-yl)phenyl)-2-oxo-oxazolidin-5-yl)methylamine

(R)-[N-3-[3-fluoro-4-[N-1-(4-carbobenzoxy)piperazinyl]-phenyl]-2-oxo-5-oxazolidinyl]methanol

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