(R)-3-Hydroxy-2-methyl-2-((R)-2-oxo-4-phenyl-oxazolidin-3-yl)-propionic acid

Base Information

• Chemical Name: (R)-3-Hydroxy-2-methyl-2-((R)-2-oxo-4-phenyl-oxazolidin-3-yl)-propionic acid
• CAS No.: 151075-01-3
• Molecular Formula: C₁₃H₁₅NO₅
• Molecular Weight: 265.266
• Mol file: 151075-01-3.mol

Synonyms:(R)-3-Hydroxy-2-methyl-2-((R)-2-oxo-4-phenyl-oxazolidin-3-yl)-propionic acid

Chemical Property of (R)-3-Hydroxy-2-methyl-2-((R)-2-oxo-4-phenyl-oxazolidin-3-yl)-propionic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-3-Hydroxy-2-methyl-2-((R)-2-oxo-4-phenyl-oxazolidin-3-yl)-propionic acid

There total 7 articles about (R)-3-Hydroxy-2-methyl-2-((R)-2-oxo-4-phenyl-oxazolidin-3-yl)-propionic 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: 85.0%

(-)-(2R)-Methyl 3-hydroxy-2-methyl-2-<(4R)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl>propanoate (151074-99-6) → (R)-3-Hydroxy-2-methyl-2-((R)-2-oxo-4-phenyl-oxazolidin-3-yl)-propionic acid (151075-01-3)

Guidance literature:

With potassium hydroxide; In 1,4-dioxane; at 25 ℃; for 16h;

DOI:10.1021/jo00074a016

Reference yield:

(6R,7R)-7-((R)-2-Hydroxy-1-phenyl-ethylamino)-5-oxa-1-aza-bicyclo[4.2.0]octan-8-one → (R)-3-Hydroxy-2-methyl-2-((R)-2-oxo-4-phenyl-oxazolidin-3-yl)-propionic acid (151075-01-3)

Guidance literature:

Multi-step reaction with 6 steps

1: i-Pr₂NEt / CH₂Cl₂ / 0.75 h / 0 °C

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

3: HCl / methanol / 24 h / 25 °C

4: 50 percent / 1 N HCl / tetrahydrofuran / 48 h / 25 °C

5: 95 percent / NaBH₄ / methanol / 0.75 h / 0 °C

6: 85 percent / 1 M KOH / dioxane / 16 h / 25 °C

With hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; potassium hexamethylsilazane; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo00074a016

Reference yield:

(6R,7R)-7-((R)-2,2-Dimethyl-4-phenyl-oxazolidin-3-yl)-5-oxa-1-aza-bicyclo[4.2.0]octan-8-one (124716-39-8) → (R)-3-Hydroxy-2-methyl-2-((R)-2-oxo-4-phenyl-oxazolidin-3-yl)-propionic acid (151075-01-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 0.2 N HCl / tetrahydrofuran / 0.75 h / 25 °C

2: i-Pr₂NEt / CH₂Cl₂ / 0.75 h / 0 °C

3: 80 percent / KHMDS / toluene; tetrahydrofuran; dimethylformamide / 1.) -78 deg C, 1 h, 2.) -78 deg C, 15 min

4: HCl / methanol / 24 h / 25 °C

5: 50 percent / 1 N HCl / tetrahydrofuran / 48 h / 25 °C

6: 95 percent / NaBH₄ / methanol / 0.75 h / 0 °C

7: 85 percent / 1 M KOH / dioxane / 16 h / 25 °C

With hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; potassium hexamethylsilazane; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo00074a016

upstream raw materials:

(-)-(2R)-Methyl 3-hydroxy-2-methyl-2-<(4R)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl>propanoate

(6R,7R)-7-((R)-2,2-Dimethyl-4-phenyl-oxazolidin-3-yl)-5-oxa-1-aza-bicyclo[4.2.0]octan-8-one

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

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

Downstream raw materials:

(R)-(-)-2-methylserine