Ethyl bromoacetate → HCID 57786461, Verbindung

To a solution of 2-butyl-2H-benzo[b][1,4]thiazin-3(4H)-one (6.3 mmol, 1400 mg) in DMF (5 ml) was added NaH (6.9 mmol, 167 mg) and the reaction mixture was stirred at room temperature for 1 h before the dropwise addition of ethyl bromoacetate (6.3 mmol, 1052 mg). The reaction mixture was stirred at room temperature overnight, diluted with water and extracted with ethyl acetate. The organic layer was washed with 1N HCl, Sat. NaHCO3, dried over Na2SO4 and evaporated to dryness. The crude compound was dissolved in MeOH (10 ml) and 1 N NaOH (10 ml) and stirred at room temperature for 2 h. The MeOH was removed under reduced pressure and the resulting aqueous solution extracted with EtOAc. The aqueous layer was acidified to pH 2 with 1N HCl and extracted with EtOAc. The organic phase was dried over Na2SO4 and the solvent was evaporated to give the title compound. LC/MS (10% to 99%): M/Z (M+H)+ (obs)=280.2; tR=3.01.

1. extractionextracted with ethyl acetate
2. washThe organic layer was washed with 1N HCl, Sat. NaHCO3
3. dry with materialdried over Na2SO4
4. customevaporated to dryness
5. dissolutionThe crude compound was dissolved in MeOH (10 ml)
6. stirring1 N NaOH (10 ml) and stirred at room temperature for 2 h
7. customThe MeOH was removed under reduced pressure
8. extractionthe resulting aqueous solution extracted with EtOAc
9. extractionextracted with EtOAc
10. dry with materialThe organic phase was dried over Na2SO4
11. customthe solvent was evaporated

ORD-Eintrag

ord-1b4af71c4ebb44e0bec2a8626f08248b

Quelldatensatz

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07842686B2