{[(3S,11aR)-8-({[(2,4-difluorophenyl)methyl]amino}carbonyl)-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydro[1,3]oxazolo[3,2-a]pyrido[1,2-d]pyrazin-6-yl]oxy}methyl methyl carbonate

Base Information

• Chemical Name: {[(3S,11aR)-8-({[(2,4-difluorophenyl)methyl]amino}carbonyl)-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydro[1,3]oxazolo[3,2-a]pyrido[1,2-d]pyrazin-6-yl]oxy}methyl methyl carbonate
• CAS No.: 1206168-05-9
• Molecular Formula: C₂₂H₂₁F₂N₃O₈
• Molecular Weight: 493.421
• Mol file: 1206168-05-9.mol

Synonyms:{[(3S,11aR)-8-({[(2,4-difluorophenyl)methyl]amino}carbonyl)-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydro[1,3]oxazolo[3,2-a]pyrido[1,2-d]pyrazin-6-yl]oxy}methyl methyl carbonate

Chemical Property of {[(3S,11aR)-8-({[(2,4-difluorophenyl)methyl]amino}carbonyl)-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydro[1,3]oxazolo[3,2-a]pyrido[1,2-d]pyrazin-6-yl]oxy}methyl methyl carbonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {[(3S,11aR)-8-({[(2,4-difluorophenyl)methyl]amino}carbonyl)-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydro[1,3]oxazolo[3,2-a]pyrido[1,2-d]pyrazin-6-yl]oxy}methyl methyl carbonate

There total 13 articles about {[(3S,11aR)-8-({[(2,4-difluorophenyl)methyl]amino}carbonyl)-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydro[1,3]oxazolo[3,2-a]pyrido[1,2-d]pyrazin-6-yl]oxy}methyl methyl carbonate 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:

iodomethyl methyl carbonate (69862-08-4) + (3S,11aR)-N-[(2,4-difluorophenyl)methyl]-3-methyl-5,7-dioxo-6-[(phenylmethyl)oxy]-2,3,5,7,11,11a-hexahydro[1,3]oxazolo[3,2-a]pyrido[1,2-d]pyrazine-8-carboxamide sodium salt → {[(3S,11aR)-8-({[(2,4-difluorophenyl)methyl]amino}carbonyl)-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydro[1,3]oxazolo[3,2-a]pyrido[1,2-d]pyrazin-6-yl]oxy}methyl methyl carbonate (1206168-05-9)

Guidance literature:

(3S,11aR)-N-[(2,4-difluorophenyl)methyl]-3-methyl-5,7-dioxo-6-[(phenylmethyl)oxy]-2,3,5,7,11,11a-hexahydro[1,3]oxazolo[3,2-a]pyrido[1,2-d]pyrazine-8-carboxamide sodium salt; With tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate; In dichloromethane; water; for 0.0833333h;

iodomethyl methyl carbonate; In dichloromethane; water; for 3h;

Reference yield:

2-[(E)-2-phenylethenyl]-3-[(phenylmethyl)oxy]-4H-pyran-4-one (1206102-05-7) → {[(3S,11aR)-8-({[(2,4-difluorophenyl)methyl]amino}carbonyl)-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydro[1,3]oxazolo[3,2-a]pyrido[1,2-d]pyrazin-6-yl]oxy}methyl methyl carbonate (1206168-05-9)

Guidance literature:

Multi-step reaction with 10 steps

1.1: sodium periodate; rhodium(III) chloride hydrate; water / acetonitrile; ethyl acetate / 1 h / 25 °C

1.2: 1 h / 25 °C

2.1: pyridine / ethanol / 8.5 h / 65 - 80 °C

3.1: sodium hydrogencarbonate / 1-methyl-pyrrolidin-2-one; water / 4 h / 20 °C

4.1: sodium periodate; acetic acid; water / acetonitrile / 2 h / 20 °C

5.1: acetic acid / acetonitrile; methanol / 4 h / 70 °C

6.1: N-Bromosuccinimide / 1-methyl-pyrrolidin-2-one / 2.5 h / 20 °C

7.1: N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / dimethyl sulfoxide / 9 h / 90 °C

8.1: hydrogen; palladium 10% on activated carbon / tetrahydrofuran; methanol / 3.33 h

9.1: sodium hydroxide / ethanol; water / 75 °C / Heating

10.1: potassium carbonate; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 0.08 h

10.2: 3 h

With pyridine; sodium periodate; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; rhodium(III) chloride hydrate; palladium 10% on activated carbon; water; hydrogen; tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate; potassium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; acetonitrile;

Reference yield:

1-(2,3-dihydroxypropyl)-4-oxo-3-[(phenylmethyl)oxy]-1,4-dihydro-2-pyridinecarboxylic acid (1206102-06-8) → {[(3S,11aR)-8-({[(2,4-difluorophenyl)methyl]amino}carbonyl)-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydro[1,3]oxazolo[3,2-a]pyrido[1,2-d]pyrazin-6-yl]oxy}methyl methyl carbonate (1206168-05-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: sodium hydrogencarbonate / 1-methyl-pyrrolidin-2-one; water / 4 h / 20 °C

2.1: sodium periodate; acetic acid; water / acetonitrile / 2 h / 20 °C

3.1: acetic acid / acetonitrile; methanol / 4 h / 70 °C

4.1: N-Bromosuccinimide / 1-methyl-pyrrolidin-2-one / 2.5 h / 20 °C

5.1: N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / dimethyl sulfoxide / 9 h / 90 °C

6.1: hydrogen; palladium 10% on activated carbon / tetrahydrofuran; methanol / 3.33 h

7.1: sodium hydroxide / ethanol; water / 75 °C / Heating

8.1: potassium carbonate; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 0.08 h

8.2: 3 h

With sodium periodate; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium 10% on activated carbon; water; hydrogen; tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate; potassium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; acetonitrile;

upstream raw materials:

iodomethyl methyl carbonate

2-(2-hydroxy-2-phenylethyl)-3-[(phenylmethyl)oxy]-4H-pyran-4-one

3-(benzyloxy)-1-((tert-butoxycarbonyl)amino)-4-oxo-1,4-dihydropyridine-2-carboxylic acid ethyl ester

2-[(E)-2-phenylethenyl]-3-[(phenylmethyl)oxy]-4H-pyran-4-one

Refernces