(3S,11aR)-6-methoxy-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydrooxazolo[3,2-d]pyrido[1,2-a]pyrazine-8-carboxylic acid

Base Information

• Chemical Name: (3S,11aR)-6-methoxy-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydrooxazolo[3,2-d]pyrido[1,2-a]pyrazine-8-carboxylic acid
• CAS No.: 1335210-24-6
• Molecular Formula: C13H14N2O6
• Molecular Weight: 294.264
• Mol file: 1335210-24-6.mol

Synonyms:Oxazolo[3,2-a]pyrido[1,2-d]pyrazine-8-carboxylic acid, 2,3,5,7,11,11a-hexahydro-6-methoxy-3-methyl-5,7-dioxo-, (3S,11aR)-;(3S,11aR)-N-[(2,4-difluorophenyl)methyl]-3-methyl-6-(methyloxy)-5,7-dioxo-2,3,5,7,11,11a-hexahydro[1,3]oxazolo[3,2-a]pyrido[1,2-d]pyrazine-8-carboxamide

Chemical Property of (3S,11aR)-6-methoxy-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydrooxazolo[3,2-d]pyrido[1,2-a]pyrazine-8-carboxylic acid

Chemical Property:

• Boiling Point: 556.1±50.0 °C(Predicted)
• PKA: 5.46±0.40(Predicted)
• PSA: 98.07000
• Density: 1.56±0.1 g/cm3(Predicted)
• LogP: -0.30640
• Storage Temp.: Sealed in dry,Room Temperature

Purity/Quality:

98% min ^*data from raw suppliers

(3S,11AR)-6-methoxy-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydrooxazolo[3,2-a]pyrido[1,2-d]pyrazine-8-carboxylicacid 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (3S,11aR)-6-methoxy-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydrooxazolo[3,2-d]pyrido[1,2-a]pyrazine-8-carboxylic acid

There total 15 articles about (3S,11aR)-6-methoxy-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydrooxazolo[3,2-d]pyrido[1,2-a]pyrazine-8-carboxylic acid 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:

(S)-Alaninol (2749-11-3) + 1-[2,2-bis(methyloxy)ethyl]-5-(methyloxy)-6-[(methyloxy)carbonyl]-4-oxo-1,4-dihydro-3-pyridinecarboxylic acid (1335210-23-5) → (3S,11aR)-3-methyl-6-(methyloxy)-5,7-dioxo-2,3,5,7,11,11a-hexahydro[1,3]oxazolo[3,2-a]pyrido[1,2-d]pyrazine-8-carboxylic acid (1335210-24-6)

Guidance literature:

1-[2,2-bis(methyloxy)ethyl]-5-(methyloxy)-6-[(methyloxy)carbonyl]-4-oxo-1,4-dihydro-3-pyridinecarboxylic acid; With acetic acid; methanesulfonic acid; In acetonitrile; at 58 - 65 ℃; for 19.5h;

(S)-Alaninol; at 64 ℃; for 16.5h;

Reference yield:

(S)-1-amino-2-propanol (2799-17-9) + 1-[2,2-bis(methyloxy)ethyl]-5-(methyloxy)-6-[(methyloxy)carbonyl]-4-oxo-1,4-dihydro-3-pyridinecarboxylic acid (1335210-23-5) → (3S,11aR)-3-methyl-6-(methyloxy)-5,7-dioxo-2,3,5,7,11,11a-hexahydro[1,3]oxazolo[3,2-a]pyrido[1,2-d]pyrazine-8-carboxylic acid (1335210-24-6)

Guidance literature:

1-[2,2-bis(methyloxy)ethyl]-5-(methyloxy)-6-[(methyloxy)carbonyl]-4-oxo-1,4-dihydro-3-pyridinecarboxylic acid; With formic acid; at 65 ℃; for 3h; Inert atmosphere;

(S)-1-amino-2-propanol; With magnesium triflate; In acetonitrile; for 36h; Reflux;

Reference yield:

methyl 2-(((2,2-dimethoxyethyl)amino)methylene)-4-methoxy-3-oxobutanoate (1335210-26-8) → (3S,11aR)-3-methyl-6-(methyloxy)-5,7-dioxo-2,3,5,7,11,11a-hexahydro[1,3]oxazolo[3,2-a]pyrido[1,2-d]pyrazine-8-carboxylic acid (1335210-24-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: lithium hydride / methanol / 14 h / -25 - 40 °C

1.2: 1 h / -5 - 5 °C

1.3: -5 °C

2.1: acetic acid / methanesulfonic acid / acetonitrile / 19.5 h / 58 - 65 °C

2.2: 16.5 h / 64 °C

With lithium hydride; acetic acid; methanesulfonic acid; In methanol; acetonitrile;

upstream raw materials:

(S)-Alaninol

1-[2,2-bis(methyloxy)ethyl]-5-(methyloxy)-6-[(methyloxy)carbonyl]-4-oxo-1,4-dihydro-3-pyridinecarboxylic acid

4-methoxyacetoacetic acid methylester

methyl 2-[(dimethylamino)methylene]-4-methoxy-3-oxobutanoate

Downstream raw materials:

(4R,12aS)-N-(2,4-difluorobenzyl)-7-methoxy-4-methyl-6,8-dioxo-3,4,6,8,12,12a-hexahydro-2H-pyrido[1’,2’:4,5]pyrazino[2,1-b]oxazine-9-carboxamide

(3S,11aR)-N-[(2,4-difluorophenyl)methyl]-6-hydroxy-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydro[1,3]oxazolo[3,2-a]pyrido[1,2-d]pyrazine-8-carboxamide

Refernces

• 1、 -. "CONTINUES FLOW PROCESS FOR THE PREPARATION OF ACTIVE PHARMACEUTICAL INGREDIENTS - POLYCYCLIC CARBAMOYL PYRIDONE DERIVATIVES AND INTERMEDIATES THEREOF". . . Retrieved 2019/09/04.
• 2、 -. "PROCESS FOR PREPARING CARBAMOYLPYRIDONE DERIVATIVES AND INTERMEDIATES". Page/Page column 9. . Retrieved 2011/10/13.