(2S)-N-{(1S)-2-[4-(cyclohexylmethoxy)phenyl]-1-(1,3-dioxolan-2-yl)ethyl}-2-hydroxy-4-methylpentanamide

Base Information

• Chemical Name: (2S)-N-{(1S)-2-[4-(cyclohexylmethoxy)phenyl]-1-(1,3-dioxolan-2-yl)ethyl}-2-hydroxy-4-methylpentanamide
• CAS No.: 611210-40-3
• Molecular Formula: C₂₄H₃₇NO₅
• Molecular Weight: 419.561
• Mol file: 611210-40-3.mol

Synonyms:(2S)-N-{(1S)-2-[4-(cyclohexylmethoxy)phenyl]-1-(1,3-dioxolan-2-yl)ethyl}-2-hydroxy-4-methylpentanamide

Chemical Property of (2S)-N-{(1S)-2-[4-(cyclohexylmethoxy)phenyl]-1-(1,3-dioxolan-2-yl)ethyl}-2-hydroxy-4-methylpentanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-N-{(1S)-2-[4-(cyclohexylmethoxy)phenyl]-1-(1,3-dioxolan-2-yl)ethyl}-2-hydroxy-4-methylpentanamide

There total 7 articles about (2S)-N-{(1S)-2-[4-(cyclohexylmethoxy)phenyl]-1-(1,3-dioxolan-2-yl)ethyl}-2-hydroxy-4-methylpentanamide 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: 73.0%

(S)-2-hydroxyl-3,3-dimethylbutyric acid (13748-90-8,498-36-2) + (1S)-2-[4-(cyclohexylmethoxy)phenyl]-1-(1,3-dioxolan-2-yl)ethanamine (611210-24-3) → (2S)-N-{(1S)-2-[4-(cyclohexylmethoxy)phenyl]-1-(1,3-dioxolan-2-yl)ethyl}-2-hydroxy-4-methylpentanamide (611210-40-3)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; for 18h;

DOI:10.1016/j.bmc.2003.09.031

Reference yield:

N-(benzyloxycarbonyl)-L-tyrosine methyl ester (13512-31-7) → (2S)-N-{(1S)-2-[4-(cyclohexylmethoxy)phenyl]-1-(1,3-dioxolan-2-yl)ethyl}-2-hydroxy-4-methylpentanamide (611210-40-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 77 percent / K₂CO₃ / dimethylformamide / 18 h / 20 °C

2: 42 percent / LiCl; NaBH₄ / tetrahydrofuran; ethanol / 18 h / 20 °C

3: 83 percent / ethyldiisopropylamine; SO₃/pyridine / CH₂Cl₂; dimethylsulfoxide / 0.5 h / cooling

4: 48 percent / pyridinium tosylate / toluene / 18 h / 80 °C

5: 81 percent / H₂ / Pd/C / ethyl acetate / 18 h / 20 °C / atmospheric pressure

6: 73 percent / benzotriazol-1-ol; Et₃N; 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide*HCl / dimethylformamide; CH₂Cl₂ / 18 h / 20 °C

With pyridine; sodium tetrahydroborate; sulfur trioxide; hydrogen; pyridinium p-toluenesulfonate; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.bmc.2003.09.031

Reference yield:

L-tyrosine methyl ester HCl (3417-91-2) → (2S)-N-{(1S)-2-[4-(cyclohexylmethoxy)phenyl]-1-(1,3-dioxolan-2-yl)ethyl}-2-hydroxy-4-methylpentanamide (611210-40-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 90 percent / Et₃N / tetrahydrofuran / 18 h / 20 °C

2: 77 percent / K₂CO₃ / dimethylformamide / 18 h / 20 °C

3: 42 percent / LiCl; NaBH₄ / tetrahydrofuran; ethanol / 18 h / 20 °C

4: 83 percent / ethyldiisopropylamine; SO₃/pyridine / CH₂Cl₂; dimethylsulfoxide / 0.5 h / cooling

5: 48 percent / pyridinium tosylate / toluene / 18 h / 80 °C

6: 81 percent / H₂ / Pd/C / ethyl acetate / 18 h / 20 °C / atmospheric pressure

7: 73 percent / benzotriazol-1-ol; Et₃N; 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide*HCl / dimethylformamide; CH₂Cl₂ / 18 h / 20 °C

With pyridine; sodium tetrahydroborate; sulfur trioxide; hydrogen; pyridinium p-toluenesulfonate; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.bmc.2003.09.031

upstream raw materials:

(S)-2-hydroxyl-3,3-dimethylbutyric acid

(1S)-2-[4-(cyclohexylmethoxy)phenyl]-1-(1,3-dioxolan-2-yl)ethanamine

N-(benzyloxycarbonyl)-L-tyrosine methyl ester

L-tyrosine methyl ester HCl

Refernces