Hydrochloric Acid → HCID 82338196, compound

Temperature

0 °C

To a suspension of NaH (0.3 g, 0.01 mol) in dry DMF (15 mL) was added TBDMS-6-(hydroxymethyl)2H-1,4-benzoxazin-3(4H)-one (2 g, 0.0068 mol) at 0° C. with stirring and allowed to stir at RT for 2 h. The reaction mixture was cooled to 0° C., added methylchloroacetate (1 g, 0.0088 mol) and stirred at RT for 12 h. The reaction mixture was further cooled to 0° C., added 50 mL of 1.5N HCl solution and stirred at RT for 12 h. The reaction mixture was diluted with water (200 mL), extracted with ethylacetate (3×150 mL). The combined organic layer was washed with 10% aqueous NaHCO3 solution, brine and dried. The solvent was removed under vacuum and crude purified by column chromatography over silica gel (CHCl3/Methanol, 99.5:0.5) to give methyl-[6-(hydroxymethyl)-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl]acetate (1.2 g, 70%).

1. stirringto stir at RT for 2 h
2. stirringstirred at RT for 12 h
3. temperatureThe reaction mixture was further cooled to 0° C.
4. stirringstirred at RT for 12 h
5. extractionextracted with ethylacetate (3×150 mL)
6. washThe combined organic layer was washed with 10% aqueous NaHCO3 solution, brine
7. customdried
8. customThe solvent was removed under vacuum and crude
9. custompurified by column chromatography over silica gel (CHCl3/Methanol, 99.5:0.5)

ORD record

ord-b92cfa17fa7b4bbca4a6e9538276622d

Source dataset

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07846925B2