(1aS,5aS)-2-(4-oxypyrazin-2-yl)-1a,2,5,5a-tetrahydro-1H-2,3-diazacyclopropa[a]pentalene-4-carboxylic acid ((S)-1-hydroxymethyl-2,2-dimethylpropyl)amide

Base Information

• Chemical Name: (1aS,5aS)-2-(4-oxypyrazin-2-yl)-1a,2,5,5a-tetrahydro-1H-2,3-diazacyclopropa[a]pentalene-4-carboxylic acid ((S)-1-hydroxymethyl-2,2-dimethylpropyl)amide
• CAS No.: 1268881-20-4
• Molecular Formula: C₁₈H₂₃N₅O₃
• Molecular Weight: 357.412
• Mol file: 1268881-20-4.mol

Synonyms:

Chemical Property of (1aS,5aS)-2-(4-oxypyrazin-2-yl)-1a,2,5,5a-tetrahydro-1H-2,3-diazacyclopropa[a]pentalene-4-carboxylic acid ((S)-1-hydroxymethyl-2,2-dimethylpropyl)amide

Chemical Property:

• Boiling Point: 636.6±55.0 °C(Predicted)
• Density: 1.49±0.1 g/cm3(Predicted)

Purity/Quality:

97% ^*data from raw suppliers

(2S,4S)-N-[(2S)-1-Hydroxy-3,3-dimethylbutan-2-yl]-9-(4-oxidopyrazin-4-ium-2-yl)-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene-7-carboxamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1aS,5aS)-2-(4-oxypyrazin-2-yl)-1a,2,5,5a-tetrahydro-1H-2,3-diazacyclopropa[a]pentalene-4-carboxylic acid ((S)-1-hydroxymethyl-2,2-dimethylpropyl)amide

There total 9 articles about (1aS,5aS)-2-(4-oxypyrazin-2-yl)-1a,2,5,5a-tetrahydro-1H-2,3-diazacyclopropa[a]pentalene-4-carboxylic acid ((S)-1-hydroxymethyl-2,2-dimethylpropyl)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: 74.9%

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) + (S)-tert-leucinol (112245-13-3) → (1aS,5aS)-2-(4-oxypyrazin-2-yl)-1a,2,5,5a-tetrahydro-1H-2,3-diazacyclopropa[a]pentalene-4-carboxylic acid ((S)-1-hydroxymethyl-2,2-dimethylpropyl)amide (1268881-20-4)

Guidance literature:

3-((4aS,5aS)-3-carboxy-4,4a,5,5a-tetrahydro-1H-cyclopropa[4,5]cyclopenta[1,2-c]pyrazol-1-yl)pyrazine 1-oxide; With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In acetonitrile; at 0 - 5 ℃; for 0.75h; Large scale;

(S)-tert-leucinol; In acetonitrile; at 0 - 5 ℃; Large scale;

Reference yield:

(4aS,5aS)-N-((S)-1-hydroxy-3,3-dimethylbutan-2-yl)-1-(pyrazin-2-yl)-4,4a,5,5a-tetrahydro-1H-cyclopropa[4,5]cyclopenta[1,2-c]pyrazole-3-carboxamide (1268881-17-9) → (1aS,5aS)-2-(4-oxypyrazin-2-yl)-1a,2,5,5a-tetrahydro-1H-2,3-diazacyclopropa[a]pentalene-4-carboxylic acid ((S)-1-hydroxymethyl-2,2-dimethylpropyl)amide (1268881-20-4)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In chloroform; at 20 - 23 ℃; for 21h;

Reference yield:

(1S,5R)-bicyclo[3.1.0]hexan-2-one (196488-92-3) → (1aS,5aS)-2-(4-oxypyrazin-2-yl)-1a,2,5,5a-tetrahydro-1H-2,3-diazacyclopropa[a]pentalene-4-carboxylic acid ((S)-1-hydroxymethyl-2,2-dimethylpropyl)amide (1268881-20-4)

Guidance literature:

Multi-step reaction with 4 steps

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

1.2: 1.5 h / 50 °C

2.1: sodium hydroxide; water / tetrahydrofuran; methanol / 20 h / 23 °C

3.1: formic acid; dihydrogen peroxide / water / 4 h / 20 - 64 °C

4.1: triethylamine; HATU / N,N-dimethyl-formamide / 1 h / 23 °C

With formic acid; potassium tert-butylate; water; dihydrogen peroxide; triethylamine; HATU; sodium hydroxide; In tetrahydrofuran; methanol; ethanol; water; N,N-dimethyl-formamide;

upstream raw materials:

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

(S)-tert-leucinol

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

(4aS,5aS)-1-(pyrazin-2-yl)-4,4a,5,5a-tetrahydro-1H-cyclopropa[4,5]cyclopenta[1,2-c]pyrazole-3-carboxylic acid