(1aS,5aS)-2-(4-oxy-pyrazin-2-yl)-1a,2,5,5a-tetrahydro-1H-2,3-diazacyclopropa[a]pentalene-4-carboxylic acid ((S)-2-hydroxy-1-phenyl-ethyl)-amide

Base Information

• Chemical Name: (1aS,5aS)-2-(4-oxy-pyrazin-2-yl)-1a,2,5,5a-tetrahydro-1H-2,3-diazacyclopropa[a]pentalene-4-carboxylic acid ((S)-2-hydroxy-1-phenyl-ethyl)-amide
• CAS No.: 1268882-21-8
• Molecular Formula: C₂₀H₁₉N₅O₃
• Molecular Weight: 377.403
• Mol file: 1268882-21-8.mol

Synonyms:

Chemical Property of (1aS,5aS)-2-(4-oxy-pyrazin-2-yl)-1a,2,5,5a-tetrahydro-1H-2,3-diazacyclopropa[a]pentalene-4-carboxylic acid ((S)-2-hydroxy-1-phenyl-ethyl)-amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1aS,5aS)-2-(4-oxy-pyrazin-2-yl)-1a,2,5,5a-tetrahydro-1H-2,3-diazacyclopropa[a]pentalene-4-carboxylic acid ((S)-2-hydroxy-1-phenyl-ethyl)-amide

There total 6 articles about (1aS,5aS)-2-(4-oxy-pyrazin-2-yl)-1a,2,5,5a-tetrahydro-1H-2,3-diazacyclopropa[a]pentalene-4-carboxylic acid ((S)-2-hydroxy-1-phenyl-ethyl)-amide 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:

3-((4aS,5aS)-3-carboxy-4,4a,5,5a-tetrahydro-1H-cyclopropa[4,5]cyclopenta[1,2-c]pyrazol-1-yl)pyrazine 1-oxide (1268883-00-6) + (2S)-2-phenylglycinol (20989-17-7) → (1aS,5aS)-2-(4-oxy-pyrazin-2-yl)-1a,2,5,5a-tetrahydro-1H-2,3-diazacyclopropa[a]pentalene-4-carboxylic acid ((S)-2-hydroxy-1-phenyl-ethyl)-amide (1268882-21-8)

Guidance literature:

With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1021/acsmedchemlett.7b00396

Reference yield:

(1R,2R,5S)-bicyclo[3.1.0]hexan-2-ol (822-58-2,822-59-3,41413-37-0,57954-54-8) → (1aS,5aS)-2-(4-oxy-pyrazin-2-yl)-1a,2,5,5a-tetrahydro-1H-2,3-diazacyclopropa[a]pentalene-4-carboxylic acid ((S)-2-hydroxy-1-phenyl-ethyl)-amide (1268882-21-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; dipotassium hydrogenphosphate; potassium dihydrogenphosphate; potassium bromide / tert-butyl methyl ether; water / -20 - 0 °C / pH Ca_. 9

1.2: 2.17 h / -10 - 0 °C

2.1: potassium tert-butylate / ethanol; tetrahydrofuran / 3.75 h / 40 - 43 °C

2.2: 1.5 h / 50 °C

3.1: methanol; water; tetrahydrofuran / 20 h / 23 °C / Alkaline conditions

4.1: dihydrogen peroxide; formic acid / water / 3 h / 58 - 64 °C

5.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 20 °C

With dipotassium hydrogenphosphate; potassium dihydrogenphosphate; formic acid; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium tert-butylate; dihydrogen peroxide; triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; potassium bromide; In tetrahydrofuran; methanol; ethanol; tert-butyl methyl ether; water; N,N-dimethyl-formamide;

DOI:10.1021/acsmedchemlett.7b00396

Reference yield:

(1S,5R)-bicyclo[3.1.0]hexan-2-one (196488-92-3) → (1aS,5aS)-2-(4-oxy-pyrazin-2-yl)-1a,2,5,5a-tetrahydro-1H-2,3-diazacyclopropa[a]pentalene-4-carboxylic acid ((S)-2-hydroxy-1-phenyl-ethyl)-amide (1268882-21-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium tert-butylate / ethanol; tetrahydrofuran / 3.75 h / 40 - 43 °C

1.2: 1.5 h / 50 °C

2.1: methanol; water; tetrahydrofuran / 20 h / 23 °C / Alkaline conditions

3.1: dihydrogen peroxide; formic acid / water / 3 h / 58 - 64 °C

4.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 20 °C

With formic acid; potassium tert-butylate; dihydrogen peroxide; triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In tetrahydrofuran; methanol; ethanol; water; N,N-dimethyl-formamide;

DOI:10.1021/acsmedchemlett.7b00396

upstream raw materials:

(1S,5R)-bicyclo[3.1.0]hexan-2-one

(1aS,5aS)-2-(pyrazin-2-yl)-1a,2,5,5a-tetrahydro-1H-2,3-diazacyclopropa[a]pentalene-4-carboxylic acid ethyl ester

3-((4aS,5aS)-3-carboxy-4,4a,5,5a-tetrahydro-1H-cyclopropa[4,5]cyclopenta[1,2-c]pyrazol-1-yl)pyrazine 1-oxide

(2S)-2-phenylglycinol