methyl (S)-{2-((3R,4aR,9aS)-4a-hydroxy-2-oxo-3-(4-oxoquinazolin-3(4H)-yl)-2,3,4,4a,9,9a-hexahydro-1H-pyrido[2,3]indol-1-yl)propanoate}

Base Information

• Chemical Name: methyl (S)-{2-((3R,4aR,9aS)-4a-hydroxy-2-oxo-3-(4-oxoquinazolin-3(4H)-yl)-2,3,4,4a,9,9a-hexahydro-1H-pyrido[2,3]indol-1-yl)propanoate}
• CAS No.: 1558046-41-5
• Molecular Formula: C₂₃H₂₂N₄O₅
• Molecular Weight: 434.451
• Mol file: 1558046-41-5.mol

Synonyms:

Chemical Property of methyl (S)-{2-((3R,4aR,9aS)-4a-hydroxy-2-oxo-3-(4-oxoquinazolin-3(4H)-yl)-2,3,4,4a,9,9a-hexahydro-1H-pyrido[2,3]indol-1-yl)propanoate}

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (S)-{2-((3R,4aR,9aS)-4a-hydroxy-2-oxo-3-(4-oxoquinazolin-3(4H)-yl)-2,3,4,4a,9,9a-hexahydro-1H-pyrido[2,3]indol-1-yl)propanoate}

There total 3 articles about methyl (S)-{2-((3R,4aR,9aS)-4a-hydroxy-2-oxo-3-(4-oxoquinazolin-3(4H)-yl)-2,3,4,4a,9,9a-hexahydro-1H-pyrido[2,3]indol-1-yl)propanoate} 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: 47.0%

(S)-2-[(R)-3-(1H-indol-3-yl)-2-(4-oxo-4H-quinazolin-3-yl)-proprionylamino]propionic acid methyl ester (1173180-37-4) → chaetominine (918659-56-0) + methyl (S)-{2-((3R,4aR,9aS)-4a-hydroxy-2-oxo-3-(4-oxoquinazolin-3(4H)-yl)-2,3,4,4a,9,9a-hexahydro-1H-pyrido[2,3]indol-1-yl)propanoate} (1558046-41-5)

Guidance literature:

(S)-2-[(R)-3-(1H-indol-3-yl)-2-(4-oxo-4H-quinazolin-3-yl)-proprionylamino]propionic acid methyl ester; With 3,3-dimethyldioxirane; In acetone; at -78 ℃; for 1h;

With methanol; potassium carbonate; In acetone; at -10 ℃; for 0.5h; Reagent/catalyst;

DOI:10.1002/cjoc.201400413

Reference yield: 42.0%

(S)-2-[(R)-3-(1H-indol-3-yl)-2-(4-oxo-4H-quinazolin-3-yl)-proprionylamino]propionic acid methyl ester (1173180-37-4) → chaetominine (918659-56-0) + methyl (αS,3R,4aS,9aS)-2,3,4,4a,9,9a-hexahydro-4a-hydroxy-α-methyl-2-oxo-3-(4-oxo-3(4H)-quinazolinyl)-1H-pyrido[2,3-b]indol-1-ethanoate + methyl (S)-{2-((3R,4aR,9aS)-4a-hydroxy-2-oxo-3-(4-oxoquinazolin-3(4H)-yl)-2,3,4,4a,9,9a-hexahydro-1H-pyrido[2,3]indol-1-yl)propanoate} (1558046-41-5)

Guidance literature:

(S)-2-[(R)-3-(1H-indol-3-yl)-2-(4-oxo-4H-quinazolin-3-yl)-proprionylamino]propionic acid methyl ester; With 3,3-dimethyldioxirane; In acetone; at -78 ℃; for 1h;

With sodium sulfite; In water; acetone; at -10 ℃; for 0.5h;

DOI:10.1002/cjoc.201400413

Reference yield:

C23H22N4O5 → chaetominine (918659-56-0) + methyl (αS,3R,4aS,9aS)-2,3,4,4a,9,9a-hexahydro-4a-hydroxy-α-methyl-2-oxo-3-(4-oxo-3(4H)-quinazolinyl)-1H-pyrido[2,3-b]indol-1-ethanoate + methyl (S)-{2-((3R,4aR,9aS)-4a-hydroxy-2-oxo-3-(4-oxoquinazolin-3(4H)-yl)-2,3,4,4a,9,9a-hexahydro-1H-pyrido[2,3]indol-1-yl)propanoate} (1558046-41-5)

Guidance literature:

In dimethyl sulfoxide; acetone; at 20 ℃; for 48h;

DOI:10.1039/c3cc48833k

upstream raw materials:

(S)-2-[(R)-3-(1H-indol-3-yl)-2-(4-oxo-4H-quinazolin-3-yl)-proprionylamino]propionic acid methyl ester

Downstream raw materials:

isochaetominine A

(+)-2,3,14-triepi-chaetominine