(4R)-3-{(2S)-2-phenyl-3-[N-(13-(pyrinin-3-yl)tridecyl)amino]propanoyl}-4-isopropyl-5,5-dimethyloxazolidin-2-one

Base Information

• Chemical Name: (4R)-3-{(2S)-2-phenyl-3-[N-(13-(pyrinin-3-yl)tridecyl)amino]propanoyl}-4-isopropyl-5,5-dimethyloxazolidin-2-one
• CAS No.: 1396008-65-3
• Molecular Formula: C₃₅H₅₃N₃O₃
• Molecular Weight: 563.824
• Mol file: 1396008-65-3.mol

Synonyms:(4R)-3-{(2S)-2-phenyl-3-[N-(13-(pyrinin-3-yl)tridecyl)amino]propanoyl}-4-isopropyl-5,5-dimethyloxazolidin-2-one

Chemical Property of (4R)-3-{(2S)-2-phenyl-3-[N-(13-(pyrinin-3-yl)tridecyl)amino]propanoyl}-4-isopropyl-5,5-dimethyloxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R)-3-{(2S)-2-phenyl-3-[N-(13-(pyrinin-3-yl)tridecyl)amino]propanoyl}-4-isopropyl-5,5-dimethyloxazolidin-2-one

There total 10 articles about (4R)-3-{(2S)-2-phenyl-3-[N-(13-(pyrinin-3-yl)tridecyl)amino]propanoyl}-4-isopropyl-5,5-dimethyloxazolidin-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: 71.0%

(4R)-3-{(2S)-2-phenyl-3-[N-benzyl-N-(13-(pyrinin-3-yl)tridecyl)amino]propanoyl}-4-isopropyl-5,5-dimethyloxazolidin-2-one (1396008-64-2) → (4R)-3-{(2S)-2-phenyl-3-[N-(13-(pyrinin-3-yl)tridecyl)amino]propanoyl}-4-isopropyl-5,5-dimethyloxazolidin-2-one (1396008-65-3)

Guidance literature:

With ammonium cerium (IV) nitrate; In water; acetonitrile; at 20 ℃; for 16h;

DOI:10.1039/c2cc34808j

Reference yield:

(4R)-3-[(2S)-2-phenyl-3-(N-benzylamino)propanoyl]-4-isopropyl-5,5-dimethyloxazolidin-2-one (1396008-63-1) + 13-(pyridin-3′-yl)tridecanal (133835-24-2) → (4R)-3-{(2S)-2-phenyl-3-[N-(13-(pyrinin-3-yl)tridecyl)amino]propanoyl}-4-isopropyl-5,5-dimethyloxazolidin-2-one (1396008-65-3)

Guidance literature:

With sodium tris(acetoxy)borohydride; acetic acid; In 1,2-dichloro-ethane; at 20 ℃; for 16h; Inert atmosphere;

DOI:10.1016/j.tetlet.2013.09.043

Reference yield:

(R)-3-(2-phenylacryloyl)-4-isopropyl-5,5-dimethyloxazolidin-2-one (1396008-61-9) → (4R)-3-{(2S)-2-phenyl-3-[N-(13-(pyrinin-3-yl)tridecyl)amino]propanoyl}-4-isopropyl-5,5-dimethyloxazolidin-2-one (1396008-65-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: 4 h / -78 °C

1.3: 16 h / -78 - 20 °C

2.1: ammonium cerium (IV) nitrate / water; acetonitrile / 16 h / 20 °C

3.1: sodium tris(acetoxy)borohydride; acetic acid / 1,2-dichloro-ethane / 20 °C

4.1: ammonium cerium (IV) nitrate / water; acetonitrile / 16 h / 20 °C

With n-butyllithium; ammonium cerium (IV) nitrate; sodium tris(acetoxy)borohydride; acetic acid; In tetrahydrofuran; hexane; water; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1039/c2cc34808j

upstream raw materials:

(R)-3-(2-phenylacryloyl)-4-isopropyl-5,5-dimethyloxazolidin-2-one

(4R)-3-[(2S)-2-phenyl-3-(N,N-dibenzylamino)propanoyl]-4-isopropyl-5,5-dimethyloxazolidin-2-one

(4R)-3-{(2S)-2-phenyl-3-[N-benzyl-N-(13-(pyrinin-3-yl)tridecyl)amino]propanoyl}-4-isopropyl-5,5-dimethyloxazolidin-2-one

2-phenylacrylic pivalic anhydride

Downstream raw materials:

(-)-(S)-nakinadine B

(R)-3-(2-phenylacryloyl)-4-isopropyl-5,5-dimethyloxazolidin-2-one

(4R)-3-[(2S)-2-phenyl-3-(N,N-dibenzylamino)propanoyl]-4-isopropyl-5,5-dimethyloxazolidin-2-one

(4R)-3-[(2R)-2-phenyl-3-(N,N-dibenzylamino)propanoyl]-4-isopropyl-5,5-dimethyloxazolidin-2-one