(S)-4-Benzyl-3-{2-[(R)-1-(4-hydroxy-phenyl)-2-oxo-pyrrolidin-3-yl]-propionyl}-oxazolidin-2-one

Base Information

• Chemical Name: (S)-4-Benzyl-3-{2-[(R)-1-(4-hydroxy-phenyl)-2-oxo-pyrrolidin-3-yl]-propionyl}-oxazolidin-2-one
• CAS No.: 648414-75-9
• Molecular Formula: C₂₃H₂₄N₂O₅
• Molecular Weight: 408.454
• Mol file: 648414-75-9.mol

Synonyms:(S)-4-Benzyl-3-{2-[(R)-1-(4-hydroxy-phenyl)-2-oxo-pyrrolidin-3-yl]-propionyl}-oxazolidin-2-one

Chemical Property of (S)-4-Benzyl-3-{2-[(R)-1-(4-hydroxy-phenyl)-2-oxo-pyrrolidin-3-yl]-propionyl}-oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-4-Benzyl-3-{2-[(R)-1-(4-hydroxy-phenyl)-2-oxo-pyrrolidin-3-yl]-propionyl}-oxazolidin-2-one

There total 7 articles about (S)-4-Benzyl-3-{2-[(R)-1-(4-hydroxy-phenyl)-2-oxo-pyrrolidin-3-yl]-propionyl}-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: 74.0%

(S)-4-Benzyl-3-{2-[(R)-1-(4-benzyloxy-phenyl)-2-oxo-pyrrolidin-3-yl]-propionyl}-oxazolidin-2-one (648414-71-5) → (S)-4-Benzyl-3-{2-[(R)-1-(4-hydroxy-phenyl)-2-oxo-pyrrolidin-3-yl]-propionyl}-oxazolidin-2-one (648414-75-9)

Guidance literature:

With hydrogen; palladium dihydroxide; In methanol;

DOI:10.1016/S0960-894X(03)00313-5

Reference yield:

(R)-tert-butyl 3-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)hex-5-enoate (179533-67-6) → (S)-4-Benzyl-3-{2-[(R)-1-(4-hydroxy-phenyl)-2-oxo-pyrrolidin-3-yl]-propionyl}-oxazolidin-2-one (648414-75-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 87 percent / O₃; PPh₃ / CH₂Cl₂

2: NaBH(OAc)3 / 1,2-dichloro-ethane

3: toluene / Heating

4: 100 percent / CF₃CO₂H / CH₂Cl₂

5: 83 percent / PivCl; Et₃N; BuLi / tetrahydrofuran

6: 42 percent / KHMDS / tetrahydrofuran

7: 74 percent / H₂ / Pd(OH)2/C / methanol

With n-butyllithium; hydrogen; pivaloyl chloride; potassium hexamethylsilazane; sodium tris(acetoxy)borohydride; ozone; triethylamine; triphenylphosphine; trifluoroacetic acid; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane; toluene;

DOI:10.1016/S0960-894X(03)00313-5

Reference yield:

[(R)-1-(4-Benzyloxy-phenyl)-2-oxo-pyrrolidin-3-yl]-acetic acid (300856-46-6) → (S)-4-Benzyl-3-{2-[(R)-1-(4-hydroxy-phenyl)-2-oxo-pyrrolidin-3-yl]-propionyl}-oxazolidin-2-one (648414-75-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 83 percent / PivCl; Et₃N; BuLi / tetrahydrofuran

2: 42 percent / KHMDS / tetrahydrofuran

3: 74 percent / H₂ / Pd(OH)2/C / methanol

With n-butyllithium; hydrogen; pivaloyl chloride; potassium hexamethylsilazane; triethylamine; palladium dihydroxide; In tetrahydrofuran; methanol;

DOI:10.1016/S0960-894X(03)00313-5

upstream raw materials:

(S)-4-Benzyl-3-{2-[(R)-1-(4-benzyloxy-phenyl)-2-oxo-pyrrolidin-3-yl]-propionyl}-oxazolidin-2-one

(R)-tert-butyl 3-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)hex-5-enoate

[(R)-1-(4-Benzyloxy-phenyl)-2-oxo-pyrrolidin-3-yl]-acetic acid

(R)-3-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-5-oxo-pentanoic acid tert-butyl ester

Downstream raw materials:

(S)-4-Benzyl-3-(2-{(R)-1-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-2-oxo-pyrrolidin-3-yl}-propionyl)-oxazolidin-2-one