4-[4-({1-butyl-3-[(R)-cyclohexyl(hydroxy)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undec-9-yl}methyl)phenoxy]benzoic acid

Base Information

• Chemical Name: 4-[4-({1-butyl-3-[(R)-cyclohexyl(hydroxy)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undec-9-yl}methyl)phenoxy]benzoic acid
• CAS No.: 674782-28-6
• Molecular Formula: C₃₃H₄₃N₃O₆
• Molecular Weight: 577.721
• Mol file: 674782-28-6.mol

Synonyms:

Chemical Property of 4-[4-({1-butyl-3-[(R)-cyclohexyl(hydroxy)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undec-9-yl}methyl)phenoxy]benzoic acid

Chemical Property:

• Vapor Pressure: 4.79E-27mmHg at 25°C

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-[4-({1-butyl-3-[(R)-cyclohexyl(hydroxy)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undec-9-yl}methyl)phenoxy]benzoic acid

There total 61 articles about 4-[4-({1-butyl-3-[(R)-cyclohexyl(hydroxy)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undec-9-yl}methyl)phenoxy]benzoic 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:

(3R)-1-Butyl-2,5-dioxo-3-[(1R)-1-hydroxy-1-cyclohexylmethyl]-1,4,9-triazaspiro[5.5]undecane methanesulfonate + 4-(4-formylphenoxy)benzoic acid (2509-18-4) → Aplaviroc (674782-28-6,675184-11-9)

Guidance literature:

(3R)-1-Butyl-2,5-dioxo-3-[(1R)-1-hydroxy-1-cyclohexylmethyl]-1,4,9-triazaspiro[5.5]undecane methanesulfonate; 4-(4-formylphenoxy)benzoic acid; With sodium tris(acetoxy)borohydride; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 8h;

With water; In DMF (N,N-dimethyl-formamide); at 15 - 70 ℃; for 0.666667h;

Reference yield:

(2S,3R)-3-cyclohexyloxirane-2-carbaldehyde (475056-70-3,445387-92-8) → C33H43N3O6 (674782-28-6,675184-11-9)

Guidance literature:

Multi-step reaction with 9 steps

1: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene / water; acetonitrile

2: sodium hydroxide / water

3: 20 % Pd(OH)2/C; hydrogen / methanol

4: sodium hydroxide

5: methanol / 55 °C

6: hydrogenchloride / water / 55 °C

7: acetic acid / toluene / 80 °C

8: 20 % Pd(OH)2/C; hydrogen / ethanol / 50 °C

9: sodium tris(acetoxy)borohydride; acetic acid / N,N-dimethyl-formamide

With hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; 20 % Pd(OH)2/C; hydrogen; sodium tris(acetoxy)borohydride; acetic acid; sodium hydroxide; In methanol; ethanol; water; N,N-dimethyl-formamide; toluene; acetonitrile; 5: Ugi condensation;

DOI:10.1016/j.bmcl.2010.12.109

Reference yield:

(2S,3R)-2-(t-butoxycarbonylamino)-3-cyclohexyl-3-hydroxypropanoic acid (82655-29-6) → C33H43N3O6 (674782-28-6,675184-11-9)

Guidance literature:

Multi-step reaction with 5 steps

1: methanol / 55 °C

2: hydrogenchloride / water / 55 °C

3: acetic acid / toluene / 80 °C

4: 20 % Pd(OH)2/C; hydrogen / ethanol / 50 °C

5: sodium tris(acetoxy)borohydride; acetic acid / N,N-dimethyl-formamide

With hydrogenchloride; 20 % Pd(OH)2/C; hydrogen; sodium tris(acetoxy)borohydride; acetic acid; In methanol; ethanol; water; N,N-dimethyl-formamide; toluene; 1: Ugi condensation;

DOI:10.1016/j.bmcl.2010.12.109

upstream raw materials:

4-(4-formylphenoxy)benzoic acid

(3R)-1-Butyl-2,5-dioxo-3-[(1R)-1-hydroxy-1-cyclohexylmethyl]-9-benzyl-1,4,9-triazaspiro[5.5]undecane methanesulfonate

(2R,3R)-2-benzylamino-3-cyclohexyl-3-hydroxypropanoic acid

3-cyclohexylacrylic acid methyl ester

Downstream raw materials:

C₅₆H₇₅N₁₁O₁₂

Refernces

• 1、 -. "NOVEL CRYSTALS OF TRIAZASPIRO 5.5 UNDECANE DERIVATIVE". Page/Page column 16. . Retrieved 2008/06/13.