N-[(R)-2-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-3-methyl-butyl]-benzamide

Base Information

• Chemical Name: N-[(R)-2-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-3-methyl-butyl]-benzamide
• CAS No.: 191664-12-7
• Molecular Formula: C₂₃H₂₆N₂O₄
• Molecular Weight: 394.47
• Mol file: 191664-12-7.mol

Synonyms:N-[(R)-2-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-3-methyl-butyl]-benzamide

Chemical Property of N-[(R)-2-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-3-methyl-butyl]-benzamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[(R)-2-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-3-methyl-butyl]-benzamide

There total 1 articles about N-[(R)-2-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-3-methyl-butyl]-benzamide 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: 81.0%

N-(chloromethyl)benzamide (38792-42-6) + (S)-4-benzyl-3-(3-methylbutanoyl)oxazolidin-2-one (145589-03-3,104266-90-2) → N-[(R)-2-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-3-methyl-butyl]-benzamide (191664-12-7)

Guidance literature:

With titanium tetrachloride; triethylamine; In dichloromethane; at 0 ℃; for 60h;

DOI:10.1002/hlca.19980810513

Reference yield: 77.0%

N-[(R)-2-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-3-methyl-butyl]-benzamide (191664-12-7) → (R)-2-(Benzoylamino-methyl)-3-methyl-butyric acid (210345-85-0)

Guidance literature:

With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; water; at 0 ℃; for 1h;

DOI:10.1002/hlca.19980810513

Reference yield:

N-[(R)-2-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-3-methyl-butyl]-benzamide (191664-12-7) → C46H78N6O9 (191664-19-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 77 percent / H₂O₂, LiOH*H₂O / H₂O; tetrahydrofuran / 1 h / 0 °C

2: 75 percent / aq. HCl / acetic acid / 48 h / Heating

3: 87 percent / aq. NaOH / dioxane / 16 h

4: 74 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.

5: 99 percent / H₂ / Pd/C / methanol / 18 h

6: 69 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.

With 4-methyl-morpholine; hydrogenchloride; lithium hydroxide; sodium hydroxide; hydrogen; dihydrogen peroxide; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; water; acetic acid;

DOI:10.1002/hlca.19980810513

upstream raw materials:

N-(chloromethyl)benzamide

(S)-4-benzyl-3-(3-methylbutanoyl)oxazolidin-2-one

Downstream raw materials:

(2R)-([amino]methyl)-3-methylbutanoic acid

(R)-2-(Benzoylamino-methyl)-3-methyl-butyric acid

(R)-2-(((tert-butoxycarbonyl)amino)methyl)-3-methylbutanoic acid

(R)-2-({(R)-3-[(R)-2-(tert-Butoxycarbonylamino-methyl)-3-methyl-butyrylamino]-2-methyl-propionylamino}-methyl)-4-methyl-pentanoic acid benzyl ester