N-[(S)-1-benzyl-2-hydroxyethyl]-4-(4-hydroxyphenyl)propionamide

Base Information

• Chemical Name: N-[(S)-1-benzyl-2-hydroxyethyl]-4-(4-hydroxyphenyl)propionamide
• CAS No.: 291313-46-7
• Molecular Formula: C₁₈H₂₁NO₃
• Molecular Weight: 299.37
• Mol file: 291313-46-7.mol

Synonyms:N-[(S)-1-benzyl-2-hydroxyethyl]-4-(4-hydroxyphenyl)propionamide

Chemical Property of N-[(S)-1-benzyl-2-hydroxyethyl]-4-(4-hydroxyphenyl)propionamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[(S)-1-benzyl-2-hydroxyethyl]-4-(4-hydroxyphenyl)propionamide

There total 1 articles about N-[(S)-1-benzyl-2-hydroxyethyl]-4-(4-hydroxyphenyl)propionamide 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: 54.0%

L-Phenylalaninol (3182-95-4) + 4-hydroxyphenylpropionic acid (501-97-3) → N-[(S)-1-benzyl-2-hydroxyethyl]-4-(4-hydroxyphenyl)propionamide (291313-46-7)

Guidance literature:

4-hydroxyphenylpropionic acid; With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine; In dichloromethane; for 0.5h;

L-Phenylalaninol; With triethylamine; In dichloromethane; at 0 - 20 ℃; for 10h; Further stages.;

DOI:10.1021/jo000341v

Reference yield: 57.0%

acetic anhydride (108-24-7) + N-[(S)-1-benzyl-2-hydroxyethyl]-4-(4-hydroxyphenyl)propionamide (291313-46-7) → N-[(S)-1-benzyl-2-hydroxyethyl]-3-(4-acetoxyphenyl)propionamide (291313-32-1)

Guidance literature:

In sodium hydroxide; for 0.333333h;

DOI:10.1021/jo000341v

Reference yield:

N-[(S)-1-benzyl-2-hydroxyethyl]-4-(4-hydroxyphenyl)propionamide (291313-46-7) → 1-[(S)-2'-acetoxy-1'-benzylethyl]-1-azaspiro[4.5]deca-2,8-dione

Guidance literature:

Multi-step reaction with 6 steps

1: 57 percent / aq. NaOH / 0.33 h

2: 74 percent / Burgess reagent / tetrahydrofuran / 2 h / Heating

3: 73 percent / potassium carbonate / methanol / 1 h / 20 °C

4: 50 percent Spectr_. / iodobenzene diacetate / 2,2,2-trifluoro-ethanol / 0.5 h / 25 °C

5: pyridine; 4-(dimethylamino)pyridine / 12 h / 20 °C

6: 90 percent / hydrogen / Pt on carbon / ethyl acetate / 0.33 h / 20 °C / 760.05 Torr

With pyridine; dmap; Burgess Reagent; [bis(acetoxy)iodo]benzene; hydrogen; potassium carbonate; platinum on activated charcoal; In tetrahydrofuran; methanol; sodium hydroxide; 2,2,2-trifluoroethanol; ethyl acetate; 1: Acetylation / 2: Cyclization / 3: Deacetylation / 4: Oxidation / 5: Acetylation / 6: Catalytic hydrogenation;

DOI:10.1021/jo000341v

upstream raw materials:

L-Phenylalaninol

4-hydroxyphenylpropionic acid

Downstream raw materials:

(S)-4-benzyl-2-[2-(4-hydroxyphenyl)ethyl]-2-oxazoline

N-[(S)-1-benzyl-2-hydroxyethyl]-3-(4-acetoxyphenyl)propionamide

(S)-2-[2-(4-acetoxyphenyl)ethyl]-4-benzyl-2-oxazoline

1-[(S)-2'-acetoxy-1'-benzylethyl]-1-azaspiro[4.5]deca-6,9-diene-2,8-dione