Potassium Carbonate → HCID 22916722, compound

To 570 mg (3.1 mmol) of the above-obtained 2-(methoxyacetylamino)methylthiazole was added 5 ml of phosphorus oxychloride. The mixture was refluxed for 4 hours, cooled to room temperature, and concentrated to dryness under reduced pressure. To the residue were added 2 ml of water and 5 ml of methylene chloride to obtain a solution, to which was added 2 g of potassium carbonate little by little. The mixture was stirred for 5 minutes. The organic layer was separated, and the aqueous layer was extracted two times with methylene chloride. The combined organic layers were dried over anhydrous potassium carbonate, concentrated under reduced pressure, and purified by flash column chromatography using silica gel, eluting with ethyl acetate. A fraction containing the desired compound was concentrated to dryness. The residue was further purified by column chromatography using Sephadex LH 20, eluting with a 1:1 mixture of chloroform and methanol to give 110 mg (yield 21%) of the title compound.

1. temperatureThe mixture was refluxed for 4 hours
2. concentrationconcentrated to dryness under reduced pressure
3. additionTo the residue were added 2 ml of water and 5 ml of methylene chloride
4. customto obtain a solution
5. customThe organic layer was separated
6. extractionthe aqueous layer was extracted two times with methylene chloride
7. dry with materialThe combined organic layers were dried over anhydrous potassium carbonate
8. concentrationconcentrated under reduced pressure
9. custompurified by flash column chromatography
10. washeluting with ethyl acetate
11. additionA fraction containing the desired compound
12. concentrationwas concentrated to dryness
13. customThe residue was further purified by column chromatography
14. washeluting with a 1:1 mixture of chloroform and methanol

ORD record

ord-0417985692364062bb377dbcdb24edcf

Source dataset

uspto-grants-1997_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05663162