(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.: 1361403-99-7
• Molecular Formula: C₃₇H₄₉NO₄
• Molecular Weight: 571.8
• Mol file: 1361403-99-7.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: 83.0%

4-(1-adamantyl)-N-((5-((R)-3-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-2-(cyclohexylmethyl)-3-oxopropyl)-2-propoxyphenyl)methyl)benzamide (1401791-61-4) → (R)-2-((3-(((4-(1-adamantyl)benzoyl)amino)methyl)-4-propoxyphenyl)methyl)-3-cyclohexylpropanoic acid (1361403-99-7)

Guidance literature:

With lithium hydroxide monohydrate; dihydrogen peroxide; In tetrahydrofuran; water; at 0 - 20 ℃; for 5.5h; Inert atmosphere;

DOI:10.1016/j.bmc.2012.08.061

Reference yield:

benzyl 2-propoxy-5-formylsalicylate (1259391-04-2) → (R)-2-((3-(((4-(1-adamantyl)benzoyl)amino)methyl)-4-propoxyphenyl)methyl)-3-cyclohexylpropanoic acid (1361403-99-7)

Guidance literature:

Multi-step reaction with 8 steps

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

2: phosphorus tribromide / diethyl ether / 2 h / 0 °C

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

4: 10% Pd/C; hydrogen / ethyl acetate / 1500.15 - 2250.23 Torr

5: borane-THF / 0 - 20 °C

6: pyridinium dichromate / dichloromethane / 12 h / 20 °C

7: triethylsilane; trifluoroacetic acid / toluene / 48 h / Reflux; Inert atmosphere

8: dihydrogen peroxide; lithium hydroxide monohydrate / tetrahydrofuran; water / 5.5 h / 0 - 20 °C / Inert atmosphere

With triethylsilane; sodium tetrahydroborate; borane-THF; lithium hydroxide monohydrate; 10% Pd/C; pyridinium dichromate; hydrogen; dihydrogen peroxide; sodium hexamethyldisilazane; phosphorus tribromide; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; ethyl acetate; toluene;

DOI:10.1016/j.bmc.2012.08.061

Reference yield:

benzyl 5-hydroxymethyl-2-propoxybenzoate (1259391-05-3) → (R)-2-((3-(((4-(1-adamantyl)benzoyl)amino)methyl)-4-propoxyphenyl)methyl)-3-cyclohexylpropanoic acid (1361403-99-7)

Guidance literature:

Multi-step reaction with 7 steps

1: phosphorus tribromide / diethyl ether / 2 h / 0 °C

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

3: 10% Pd/C; hydrogen / ethyl acetate / 1500.15 - 2250.23 Torr

4: borane-THF / 0 - 20 °C

5: pyridinium dichromate / dichloromethane / 12 h / 20 °C

6: triethylsilane; trifluoroacetic acid / toluene / 48 h / Reflux; Inert atmosphere

7: dihydrogen peroxide; lithium hydroxide monohydrate / tetrahydrofuran; water / 5.5 h / 0 - 20 °C / Inert atmosphere

With triethylsilane; borane-THF; lithium hydroxide monohydrate; 10% Pd/C; pyridinium dichromate; hydrogen; dihydrogen peroxide; sodium hexamethyldisilazane; phosphorus tribromide; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; dichloromethane; water; ethyl acetate; toluene;

DOI:10.1016/j.bmc.2012.08.061

upstream raw materials:

benzyl 2-propoxy-5-formylsalicylate

benzyl 5-hydroxymethyl-2-propoxybenzoate

benzyl 5-bromomethyl-2-propoxybenzoate

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