(4S)-3-[(2S,3S)-2-(biphenyl-4-ylmethoxy)-3-hydroxy-2-methyl-3-(5-methylisoxazol-3-yl)propanoyl]-5,5-dimethyl-4-phenyl-1,3-oxazolidin-2-one

Base Information

• Chemical Name: (4S)-3-[(2S,3S)-2-(biphenyl-4-ylmethoxy)-3-hydroxy-2-methyl-3-(5-methylisoxazol-3-yl)propanoyl]-5,5-dimethyl-4-phenyl-1,3-oxazolidin-2-one
• CAS No.: 1219004-82-6
• Molecular Formula: C₃₂H₃₂N₂O₆
• Molecular Weight: 540.616
• Mol file: 1219004-82-6.mol

Synonyms:(4S)-3-[(2S,3S)-2-(biphenyl-4-ylmethoxy)-3-hydroxy-2-methyl-3-(5-methylisoxazol-3-yl)propanoyl]-5,5-dimethyl-4-phenyl-1,3-oxazolidin-2-one

Chemical Property of (4S)-3-[(2S,3S)-2-(biphenyl-4-ylmethoxy)-3-hydroxy-2-methyl-3-(5-methylisoxazol-3-yl)propanoyl]-5,5-dimethyl-4-phenyl-1,3-oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S)-3-[(2S,3S)-2-(biphenyl-4-ylmethoxy)-3-hydroxy-2-methyl-3-(5-methylisoxazol-3-yl)propanoyl]-5,5-dimethyl-4-phenyl-1,3-oxazolidin-2-one

There total 5 articles about (4S)-3-[(2S,3S)-2-(biphenyl-4-ylmethoxy)-3-hydroxy-2-methyl-3-(5-methylisoxazol-3-yl)propanoyl]-5,5-dimethyl-4-phenyl-1,3-oxazolidin-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: 34.0%

→ (4S)-3-[(2S,3S)-2-(biphenyl-4-ylmethoxy)-3-hydroxy-2-methyl-3-(5-methylisoxazol-3-yl)propanoyl]-5,5-dimethyl-4-phenyl-1,3-oxazolidin-2-one (1219004-82-6)

Guidance literature:

Reference yield:

5-methyl-isoxazole-3-carbaldehyde (62254-74-4) + C27H27NO4 (1219004-56-4) → (4S)-3-[(2S,3S)-2-(biphenyl-4-ylmethoxy)-3-hydroxy-2-methyl-3-(5-methylisoxazol-3-yl)propanoyl]-5,5-dimethyl-4-phenyl-1,3-oxazolidin-2-one (1219004-82-6)

Guidance literature:

C₂₇H₂₇NO₄; With lithium diisopropyl amide; In tetrahydrofuran; n-heptane; ethylbenzene; at -78 ℃; for 0.5h; Inert atmosphere;

With triisopropoxytitanium(IV) chloride; In tetrahydrofuran; n-heptane; ethylbenzene; at -40 ℃; for 1h; Inert atmosphere;

5-methyl-isoxazole-3-carbaldehyde; In tetrahydrofuran; n-heptane; ethylbenzene; at -78 - -40 ℃; for 2h; Inert atmosphere;

DOI:10.1016/j.bmcl.2012.01.140

Reference yield:

(2S)-2-(biphenyl-4-ylmethoxy)propanoic acid (658703-75-4) → (4S)-3-[(2S,3S)-2-(biphenyl-4-ylmethoxy)-3-hydroxy-2-methyl-3-(5-methylisoxazol-3-yl)propanoyl]-5,5-dimethyl-4-phenyl-1,3-oxazolidin-2-one (1219004-82-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: thionyl chloride / 1 h / 65 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

2.2: 3.5 h / -78 - 25 °C / Inert atmosphere

3.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane; ethylbenzene / 0.5 h / -78 °C / Inert atmosphere

3.2: 1 h / -40 °C / Inert atmosphere

3.3: 2 h / -78 - -40 °C / Inert atmosphere

With n-butyllithium; thionyl chloride; lithium diisopropyl amide; In tetrahydrofuran; hexane; n-heptane; ethylbenzene;

DOI:10.1016/j.bmcl.2012.01.140

upstream raw materials:

5-methyl-isoxazole-3-carbaldehyde

C₂₇H₂₇NO₄

methyl (2S)-2-(biphenyl-4-ylmethoxy)propanoate

(2S)-2-(biphenyl-4-ylmethoxy)propanoic acid

Downstream raw materials:

(2S,3S)-2-(biphenyl-4-ylmethoxy)-N,3-dihydroxy-2-methyl-3-(5-methylisoxazol-3-yl)propanamide