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

Base Information

• Chemical Name: (R)-tert-butyl 3-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)-5-methylhexanoate
• CAS No.: 144287-83-2
• Molecular Formula: C₂₂H₃₁NO₅
• Molecular Weight: 389.492
• Mol file: 144287-83-2.mol

Synonyms:(R)-tert-butyl 3-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)-5-methylhexanoate

Chemical Property of (R)-tert-butyl 3-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)-5-methylhexanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-tert-butyl 3-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)-5-methylhexanoate

There total 7 articles about (R)-tert-butyl 3-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)-5-methylhexanoate 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: 82.0%

bromoacetic acid tert-butyl ester (5292-43-3) + (S)-4-benzyl-3-(4-methylpentanoyl)oxazolidin-2-one (113543-30-9) → (R)-tert-butyl 3-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)-5-methylhexanoate (144287-83-2)

Guidance literature:

With 1,1,1,3,3,3-hexamethyl-disilazane; at -78 ℃;

DOI:10.1016/S0960-894X(03)00214-2

Reference yield:

(S)-4-Benzyl-2-oxazolidinone (90719-32-7) → (R)-tert-butyl 3-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)-5-methylhexanoate (144287-83-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) n-BuLi / 1.) THF, - 78 deg C, 1 h, 2.) THF, a) -78 deg C, 1 h, b) RT, 1 h

2: 1.) lithium hexamethyldisilazide / 1.) THF, -78 deg C, 1 h, 2.) THF, a) -78 deg C, 1 h, b) -40 deg C, 1 h

With n-butyllithium; lithium hexamethyldisilazane;

DOI:10.1021/jm970494j

Reference yield:

4-methylvaleroyl chloride (38136-29-7) → (R)-tert-butyl 3-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)-5-methylhexanoate (144287-83-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium / tetrahydrofuran / 1.17 h / -78 °C / Inert atmosphere

1.2: 2 h / -78 - 20 °C / Inert atmosphere

2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1.17 h / Inert atmosphere

2.2: 1 h / -78 °C / Inert atmosphere

With n-butyllithium; lithium hexamethyldisilazane; In tetrahydrofuran;

DOI:10.1021/ja403523p

upstream raw materials:

bromoacetic acid tert-butyl ester

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

4-methylvaleroyl chloride

(S)-4-Benzyl-2-oxazolidinone

Downstream raw materials:

(R)-3-(cyclopropyl(4-(2-(6-methoxypyridin-3-yl)phenyl)thiazol-2-yl)carbamoyl)-5-methyl hexanoic acid

(R)-3-((4-(2-(6-(1H-pyrazol-1-yl)pyridin-3-yl)phenyl)thiazol-2-yl)(cyclopropyl)carbamoyl)-5-methylhexanoic acid

Refernces

• 1、 Hoveyda, Hamid R.,Fraser, Graeme L.,Zoute, Ludivine,Dutheuil, Guillaume,Schils, Didier,Brantis, Cyrille,Lapin, Alexey,Parcq, Julien,Guitard, Sandra,Lenoir, Fran?ois,Bousmaqui, Mohamed El,Rorive, Sarah,Hospied, Sandrine,Blanc, Sébastien,Bernard, Jér?me,Ooms, Frédéric,McNelis, Joanne C.,Olefsky, Jerrold M.. "N-Thiazolylamide-based free fatty-acid 2 receptor agonists: Discovery, lead optimization and demonstration of off-target effect in a diabetes model". . p. 5169 - 5180. Retrieved 2018/10/02.
• 2、 Song, Jiao,Peng, Peng,Chang, Jun,Liu, Ming-Ming,Yu, Jian-Ming,Zhou, Lu,Sun, Xun. "Selective non-zinc binding MMP-2 inhibitors: Novel benzamide Ilomastat analogs with anti-tumor metastasis". . p. 2174 - 2178. Retrieved 2016/04/20.