(S)-3-hydroxy-N-((S)-1-phenylethyl)-3-(1,4,5,8-tetramethoxynaphthalen-2-yl)propanamide

Base Information

• Chemical Name: (S)-3-hydroxy-N-((S)-1-phenylethyl)-3-(1,4,5,8-tetramethoxynaphthalen-2-yl)propanamide
• CAS No.: 1372122-56-9
• Molecular Formula: C₂₅H₂₉NO₆
• Molecular Weight: 439.508
• Mol file: 1372122-56-9.mol

Synonyms:(S)-3-hydroxy-N-((S)-1-phenylethyl)-3-(1,4,5,8-tetramethoxynaphthalen-2-yl)propanamide

Chemical Property of (S)-3-hydroxy-N-((S)-1-phenylethyl)-3-(1,4,5,8-tetramethoxynaphthalen-2-yl)propanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-hydroxy-N-((S)-1-phenylethyl)-3-(1,4,5,8-tetramethoxynaphthalen-2-yl)propanamide

There total 3 articles about (S)-3-hydroxy-N-((S)-1-phenylethyl)-3-(1,4,5,8-tetramethoxynaphthalen-2-yl)propanamide 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%

(S)-1-phenyl-ethylamine (2627-86-3) + 3-hydroxy-3-(1,4,5,8-tetramethoxynaphthalen-2-yl)propanoic acid (1372122-54-7) → (R)-3-hydroxy-N-((S)-1-phenylethyl)-3-(1,4,5,8-tetramethoxynaphthalen-2-yl)propanamide (1372122-55-8) + (S)-3-hydroxy-N-((S)-1-phenylethyl)-3-(1,4,5,8-tetramethoxynaphthalen-2-yl)propanamide (1372122-56-9)

Guidance literature:

With dmap; bis(2-oxo-3-oxazolidinyl)phosphane; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 3h;

DOI:10.1002/ejoc.201101505

Reference yield:

ethyl 3-hydroxy-3-(1,4,5,8-tetramethoxynaphthalen-2-yl)propanoate (438036-54-5) → (S)-3-hydroxy-N-((S)-1-phenylethyl)-3-(1,4,5,8-tetramethoxynaphthalen-2-yl)propanamide (1372122-56-9)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide / methanol; water / 2 h / 20 °C

2: dmap; bis(2-oxo-3-oxazolidinyl)phosphane; triethylamine / N,N-dimethyl-formamide / 3 h / 20 °C

With dmap; bis(2-oxo-3-oxazolidinyl)phosphane; triethylamine; sodium hydroxide; In methanol; water; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.201101505

Reference yield:

1,4,5,8-tetramethoxynaphthalene-2-carbaldehyde (88818-28-4) → (S)-3-hydroxy-N-((S)-1-phenylethyl)-3-(1,4,5,8-tetramethoxynaphthalen-2-yl)propanamide (1372122-56-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: zinc / tetrahydrofuran / 2 h / 20 °C / Reflux; Inert atmosphere

1.2: 1.17 h / 20 °C / Inert atmosphere

2.1: sodium hydroxide / methanol; water / 2 h / 20 °C

3.1: dmap; bis(2-oxo-3-oxazolidinyl)phosphane; triethylamine / N,N-dimethyl-formamide / 3 h / 20 °C

With dmap; bis(2-oxo-3-oxazolidinyl)phosphane; triethylamine; sodium hydroxide; zinc; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.201101505

upstream raw materials:

ethyl 3-hydroxy-3-(1,4,5,8-tetramethoxynaphthalen-2-yl)propanoate

(S)-1-phenyl-ethylamine

3-hydroxy-3-(1,4,5,8-tetramethoxynaphthalen-2-yl)propanoic acid

1,4,5,8-tetramethoxynaphthalene-2-carbaldehyde

Downstream raw materials:

(S)-5,8-dihydroxy-2-(1-hydroxy-4-methylpent-3-enyl)naphthalene-1,4-dione

(S)-3-(tert-butyldimethylsilyloxy)-N-((S)-1-phenylethyl)-3-(1,4,5,8-tetramethoxynaphthalen-2-yl)propanamide