(S)-4-[4-((S)-1-Benzyloxycarbonyl-2-methyl-propylamino)-benzofuran-3-ylmethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (S)-4-[4-((S)-1-Benzyloxycarbonyl-2-methyl-propylamino)-benzofuran-3-ylmethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
• CAS No.: 168335-67-9
• Molecular Formula: C₃₁H₄₀N₂O₆
• Molecular Weight: 536.668
• Mol file: 168335-67-9.mol

Synonyms:(S)-4-[4-((S)-1-Benzyloxycarbonyl-2-methyl-propylamino)-benzofuran-3-ylmethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Chemical Property of (S)-4-[4-((S)-1-Benzyloxycarbonyl-2-methyl-propylamino)-benzofuran-3-ylmethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-4-[4-((S)-1-Benzyloxycarbonyl-2-methyl-propylamino)-benzofuran-3-ylmethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

There total 12 articles about (S)-4-[4-((S)-1-Benzyloxycarbonyl-2-methyl-propylamino)-benzofuran-3-ylmethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 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: 76.0%

benzyl (R)-4-methyl-2-(trifluoromethylsulfonyloxy)pentanoate (131423-64-8) + (S)-4-(4-Amino-benzofuran-3-ylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (168335-66-8) → (S)-4-[4-((S)-1-Benzyloxycarbonyl-2-methyl-propylamino)-benzofuran-3-ylmethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (168335-67-9)

Guidance literature:

With 2,6-dimethylpyridine; In 1,2-dichloro-ethane;

Reference yield:

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine (95715-87-0) → (S)-4-[4-((S)-1-Benzyloxycarbonyl-2-methyl-propylamino)-benzofuran-3-ylmethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (168335-67-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 86 percent / benzene / 12 h / Ambient temperature

2: 61 percent / diisobutylaluminum hydride / toluene; hexane / 3 h / -60 - -40 °C

3: 78 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / Ambient temperature

4: 79 percent / palladium acetate, sodium formate, sodium carbonate, tetrabutylammonium chloride / dimethylformamide / 36 h / 80 °C

5: 76 percent / 2,6-lutidine / 1,2-dichloro-ethane / 80 °C

With 2,6-dimethylpyridine; tetrabutyl-ammonium chloride; sodium formate; palladium diacetate; diisobutylaluminium hydride; sodium carbonate; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; hexane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1021/ja00130a003

Reference yield:

N-(3-methoxyphenyl)pivalamide (56619-93-3) → (S)-4-[4-((S)-1-Benzyloxycarbonyl-2-methyl-propylamino)-benzofuran-3-ylmethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (168335-67-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) n-BuLi, 2.) bromine / 1.) THF, hexane, 0 deg C, 2.5 h, 2.) THF, hexane, -78 deg C, 1 h

2: 1.) AlCl₃ / 1.) CS₂, reflux, 3 h, 2.) 70 deg C, 2 d

3: 61 percent / ethanolic HCl / 12 h / 80 °C

4: 78 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / Ambient temperature

5: 79 percent / palladium acetate, sodium formate, sodium carbonate, tetrabutylammonium chloride / dimethylformamide / 36 h / 80 °C

6: 76 percent / 2,6-lutidine / 1,2-dichloro-ethane / 80 °C

With 2,6-dimethylpyridine; hydrogenchloride; n-butyllithium; aluminium trichloride; tetrabutyl-ammonium chloride; bromine; sodium formate; palladium diacetate; sodium carbonate; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1021/ja00130a003

upstream raw materials:

benzyl (R)-4-methyl-2-(trifluoromethylsulfonyloxy)pentanoate

(S)-4-(4-Amino-benzofuran-3-ylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

N-(3-methoxyphenyl)pivalamide

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

Refernces

• 1、 Kozikowski, Alan P.,Ma, Dawei,Du, Linh,Lewin, Nancy E.,Blumberg, Peter M.. "Effect of alteration of the heterocyclic nucleus of ILV on its isoform selectivity for PKC. Palladium-catalyzed route to benzofuran analogues of ILV". . p. 6666 - 6672. Retrieved 2007/10/02.