N-((5-((S)-2-benzyl-3-((R)-4-benzyl-2-oxo-oxazolidin-3-yl)-3-oxopropyl)-2-propoxyphenyl)methyl)-4-(1-adamantanyl)benzamide

Base Information

• Chemical Name: N-((5-((S)-2-benzyl-3-((R)-4-benzyl-2-oxo-oxazolidin-3-yl)-3-oxopropyl)-2-propoxyphenyl)methyl)-4-(1-adamantanyl)benzamide
• CAS No.: 1259391-14-4
• Molecular Formula: C₄₇H₅₂N₂O₅
• Molecular Weight: 724.94
• Mol file: 1259391-14-4.mol

Synonyms:N-((5-((S)-2-benzyl-3-((R)-4-benzyl-2-oxo-oxazolidin-3-yl)-3-oxopropyl)-2-propoxyphenyl)methyl)-4-(1-adamantanyl)benzamide

Chemical Property of N-((5-((S)-2-benzyl-3-((R)-4-benzyl-2-oxo-oxazolidin-3-yl)-3-oxopropyl)-2-propoxyphenyl)methyl)-4-(1-adamantanyl)benzamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-((5-((S)-2-benzyl-3-((R)-4-benzyl-2-oxo-oxazolidin-3-yl)-3-oxopropyl)-2-propoxyphenyl)methyl)-4-(1-adamantanyl)benzamide

There total 9 articles about N-((5-((S)-2-benzyl-3-((R)-4-benzyl-2-oxo-oxazolidin-3-yl)-3-oxopropyl)-2-propoxyphenyl)methyl)-4-(1-adamantanyl)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: 97.0%

5-((R)-2-((S)-4-benzyl-2-oxo-oxazolidine-3-carbonyl)butyl)-2-n-butoxybenzaldehyde (1259391-13-3) + 4-(1-adamantyl)benzamide (117101-74-3) → N-((5-((S)-2-benzyl-3-((R)-4-benzyl-2-oxo-oxazolidin-3-yl)-3-oxopropyl)-2-propoxyphenyl)methyl)-4-(1-adamantanyl)benzamide (1259391-14-4)

Guidance literature:

With triethylsilane; trifluoroacetic acid; In toluene; for 48h; Reflux;

DOI:10.1021/jm101233f

Reference yield:

benzyl 5-bromomethyl-2-propoxybenzoate (1259391-06-4) → N-((5-((S)-2-benzyl-3-((R)-4-benzyl-2-oxo-oxazolidin-3-yl)-3-oxopropyl)-2-propoxyphenyl)methyl)-4-(1-adamantanyl)benzamide (1259391-14-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium hexamethyldisilazane / tetrahydrofuran / -50 - -15 °C / Inert atmosphere

1.2: -50 - 20 °C / Inert atmosphere

2.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 3 h / 20 °C / 735.07 Torr

3.1: borane-THF / tetrahydrofuran / 20 °C

4.1: manganese(IV) oxide / dichloromethane / 20 °C

5.1: triethylsilane; trifluoroacetic acid / toluene / 48 h / Reflux

With triethylsilane; manganese(IV) oxide; borane-THF; palladium 10% on activated carbon; hydrogen; sodium hexamethyldisilazane; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene; 1.1: Evan's asymmetric alkylation / 1.2: Evan's asymmetric alkylation;

DOI:10.1021/jm101233f

Reference yield:

benzyl 2-propoxy-5-formylsalicylate (1259391-04-2) → N-((5-((S)-2-benzyl-3-((R)-4-benzyl-2-oxo-oxazolidin-3-yl)-3-oxopropyl)-2-propoxyphenyl)methyl)-4-(1-adamantanyl)benzamide (1259391-14-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sodium tetrahydroborate / ethanol / 0 - 20 °C

2.1: phosphorus tribromide / diethyl ether / 1.5 h / 0 °C

3.1: sodium hexamethyldisilazane / tetrahydrofuran / -50 - -15 °C / Inert atmosphere

3.2: -50 - 20 °C / Inert atmosphere

4.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 3 h / 20 °C / 735.07 Torr

5.1: borane-THF / tetrahydrofuran / 20 °C

6.1: manganese(IV) oxide / dichloromethane / 20 °C

7.1: triethylsilane; trifluoroacetic acid / toluene / 48 h / Reflux

With triethylsilane; manganese(IV) oxide; sodium tetrahydroborate; borane-THF; palladium 10% on activated carbon; hydrogen; sodium hexamethyldisilazane; phosphorus tribromide; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; ethyl acetate; toluene; 3.1: Evan's asymmetric alkylation / 3.2: Evan's asymmetric alkylation;

DOI:10.1021/jm101233f

upstream raw materials:

benzyl 5-bromomethyl-2-propoxybenzoate

benzyl 5-((S)-2-benzyl-3-((R)-4-benzyl-2-oxo-oxazolidin-3-yl)-3-oxopropyl)-2-propoxybenzoate

5-((S)-2-benzyl-3-((R)-4-benzyl-2-oxo-oxazolidin-3-yl)-3-oxopropyl)-2-propoxybenzoic acid

5-((R)-2-((S)-4-benzyl-2-oxo-oxazolidine-3-carbonyl)butyl)-2-n-butoxybenzaldehyde

Downstream raw materials:

(R)-2-((3-(((4-(1-adamantyl)benzoyl)amino)methyl)-4-propoxyphenyl)methyl)-3-cyclohexylpropanoic acid