AureusiMine A

Base Information

• Chemical Name: AureusiMine A
• CAS No.: 1244033-70-2
• Molecular Formula: C₁₄H₁₆N₂O₂
• Molecular Weight: 244.293
• Mol file: 1244033-70-2.mol

Synonyms:6-(4-hydroxybenzyl)-3-isopropylpyrazin-2(1H)-one

Chemical Property of AureusiMine A

Chemical Property:

• Melting Point: 213-215°C
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

AureusimineA ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Aureusimine A is a novel small molecule produced by a non-ribosomal peptide synthetase (NRPS) and is present in every virulent strain of S. aureus and Methicillin resistant S. aureus (MRSA) and GeneChip data shows upregulation under conditions suggestive that it is an important virulence factor.

Technology Process of AureusiMine A

There total 4 articles about AureusiMine A 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: 45.0%

C19H28N2O5 → 6-(4-hydroxybenzyl)-3-isopropylpyrazin-2(1H)-one (1244033-70-2)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1021/acs.joc.8b03206

Reference yield:

t-Boc-L-valine (13734-41-3) → 6-(4-hydroxybenzyl)-3-isopropylpyrazin-2(1H)-one (1244033-70-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 16 h / 20 °C / Inert atmosphere

2: Dess-Martin periodane / dichloromethane / 1.5 h / 20 °C

3: trifluoroacetic acid / dichloromethane / 16 h / 20 °C

With benzotriazol-1-ol; Dess-Martin periodane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/acs.joc.8b03206

Reference yield:

4-[(2S)-2-amino-3-hydroxypropyl]phenol (5034-68-4) → 6-(4-hydroxybenzyl)-3-isopropylpyrazin-2(1H)-one (1244033-70-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 16 h / 20 °C / Inert atmosphere

2: Dess-Martin periodane / dichloromethane / 1.5 h / 20 °C

3: trifluoroacetic acid / dichloromethane / 16 h / 20 °C

With benzotriazol-1-ol; Dess-Martin periodane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/acs.joc.8b03206

upstream raw materials:

t-Boc-L-valine

4-[(2S)-2-amino-3-hydroxypropyl]phenol

Refernces