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

Base Information

• Chemical Name: (R)-2-((3-(((4-(1-adamantyl)benzoyl)amino)methyl)-4-propoxyphenyl)methyl)-3-cyclohexylpropanoic acid
• CAS No.: 1259391-03-1
• Molecular Formula: C₃₇H₄₃NO₄
• Molecular Weight: 565.753
• Mol file: 1259391-03-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 10 articles about (R)-2-((3-(((4-(1-adamantyl)benzoyl)amino)methyl)-4-propoxyphenyl)methyl)-3-cyclohexylpropanoic acid 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: 86.0%

N-((5-((R)-2-benzyl-3-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-3-oxopropyl)-2-propoxyphenyl)methyl)-4-(1-adamantanyl)benzamide (1259391-10-0) → (R)-2-((3-(((4-(1-adamantyl)benzoyl)amino)methyl)-4-propoxyphenyl)methyl)-3-cyclohexylpropanoic acid (1259391-03-1)

Guidance literature:

With lithium hydrochloride monohydrate; water; dihydrogen peroxide; In tetrahydrofuran; at 0 - 20 ℃; optical yield given as %ee; Inert atmosphere;

DOI:10.1021/jm101233f

Reference yield:

benzyl 5-bromomethyl-2-propoxybenzoate (1259391-06-4) → (R)-2-((3-(((4-(1-adamantyl)benzoyl)amino)methyl)-4-propoxyphenyl)methyl)-3-cyclohexylpropanoic acid (1259391-03-1)

Guidance literature:

Multi-step reaction with 6 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

6.1: lithium hydrochloride monohydrate; water; dihydrogen peroxide / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

With triethylsilane; manganese(IV) oxide; borane-THF; lithium hydrochloride monohydrate; palladium 10% on activated carbon; water; hydrogen; dihydrogen peroxide; 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:

5-((R)-2-benzyl-3-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-3-oxopropyl)-2-propoxybenzoic acid (1259391-08-6) → (R)-2-((3-(((4-(1-adamantyl)benzoyl)amino)methyl)-4-propoxyphenyl)methyl)-3-cyclohexylpropanoic acid (1259391-03-1)

Guidance literature:

Multi-step reaction with 4 steps

1: borane-THF / tetrahydrofuran / 20 °C

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

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

4: lithium hydrochloride monohydrate; water; dihydrogen peroxide / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

With triethylsilane; manganese(IV) oxide; borane-THF; lithium hydrochloride monohydrate; water; dihydrogen peroxide; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1021/jm101233f

upstream raw materials:

benzyl 5-bromomethyl-2-propoxybenzoate

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

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

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