(S)-2-Methyl-2-((S)-2-oxo-4-phenyl-oxazolidin-3-yl)-pentanedioic acid

Base Information

• Chemical Name: (S)-2-Methyl-2-((S)-2-oxo-4-phenyl-oxazolidin-3-yl)-pentanedioic acid
• CAS No.: 151074-88-3
• Molecular Formula: C₁₅H₁₇NO₆
• Molecular Weight: 307.303
• Mol file: 151074-88-3.mol

Synonyms:(S)-2-Methyl-2-((S)-2-oxo-4-phenyl-oxazolidin-3-yl)-pentanedioic acid

Chemical Property of (S)-2-Methyl-2-((S)-2-oxo-4-phenyl-oxazolidin-3-yl)-pentanedioic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-Methyl-2-((S)-2-oxo-4-phenyl-oxazolidin-3-yl)-pentanedioic acid

There total 8 articles about (S)-2-Methyl-2-((S)-2-oxo-4-phenyl-oxazolidin-3-yl)-pentanedioic acid 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: 93.0%

(+)-(2S)-Dimethyl 2-methyl-2-<(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl>pentane-1,5-dioate (151075-02-4) → (S)-2-Methyl-2-((S)-2-oxo-4-phenyl-oxazolidin-3-yl)-pentanedioic acid (151074-88-3)

Guidance literature:

With potassium hydroxide; In 1,4-dioxane; at 25 ℃; for 48h;

DOI:10.1021/jo00074a016

Reference yield:

(6S,7S)-7-<(4S)-2-Oxo-4-phenyl-1,3-oxazolidin-3-yl>-1-aza-5-oxabicyclo<4.2.0>octan-8-one (134627-50-2) → (S)-2-Methyl-2-((S)-2-oxo-4-phenyl-oxazolidin-3-yl)-pentanedioic acid (151074-88-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 80 percent / KHMDS / toluene; tetrahydrofuran; dimethylformamide / 1.) -78 deg C, 1 h, 2.) -78 deg C, 15 min

2: HCl / methanol / 24 h / 25 °C

3: 50 percent / 1 N HCl / tetrahydrofuran / 48 h / 25 °C

4: 92 percent / tetrahydrofuran / 72 h / 25 °C

5: 85 percent / H₂ / 10percent Pd/C / methanol / 16 h / 25 °C / 1551.4 Torr

6: 93 percent / 2 M KOH / dioxane / 48 h / 25 °C

With hydrogenchloride; potassium hydroxide; hydrogen; potassium hexamethylsilazane; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo00074a016

Reference yield:

(+)-(2S)-Dimethyl 2-methyl-2-<(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl>-(3E)-pentene-1,5-dioate → (S)-2-Methyl-2-((S)-2-oxo-4-phenyl-oxazolidin-3-yl)-pentanedioic acid (151074-88-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / H₂ / 10percent Pd/C / methanol / 16 h / 25 °C / 1551.4 Torr

2: 93 percent / 2 M KOH / dioxane / 48 h / 25 °C

With potassium hydroxide; hydrogen; palladium on activated charcoal; In 1,4-dioxane; methanol;

DOI:10.1021/jo00074a016

upstream raw materials:

(+)-(2S)-Dimethyl 2-methyl-2-<(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl>pentane-1,5-dioate

(6S,7S)-7-<(4S)-2-Oxo-4-phenyl-1,3-oxazolidin-3-yl>-1-aza-5-oxabicyclo<4.2.0>octan-8-one

(+)-(2S)-Methyl 2-methyl-2-<(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl>-3-oxopropanoate

(+)-(6S,7S)-7-Methyl-7-<(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl>-1-aza-5-oxabicyclo<4.2.0>octan-8-one

Downstream raw materials:

(2S)-alpha-Methylglutamate