Water → 2-(Methoxyacetylamino)methylthiazole

To a solution of 342 mg (3.0 mmol) of 2-aminomethylthiazole and 0.50 ml (3.6 mmol) of triethylamine in 5 ml of methylene chloride was added dropwise with ice-cooling a solution of 390 mg (3.6 mmol) of methoxyacetyl chloride in 2 ml of methylene chloride, and the mixture was stirred at the temperature for 15 minutes. To this was added 2 ml of water, and 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 washed with a small amount of a50% aqueous solution of potassium carbonate, dried over anhydrous potassium carbonate, and concentrated under reduced pressure. The residue was purified by flash column chromatography using silica gel, eluting with ethyl acetate to give 570 mg of the title compound.

1. stirringthe mixture was stirred for 5 minutes
2. customThe organic layer was separated
3. extractionthe aqueous layer was extracted two times with methylene chloride
4. washThe combined organic layers were washed with a small amount of a50% aqueous solution of potassium carbonate
5. dry with materialdried over anhydrous potassium carbonate
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by flash column chromatography
8. washeluting with ethyl acetate

ORD record

ord-237e470bc8544b1394e3148d35f795cd

Source dataset

uspto-grants-1997_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05663162