Dimethyl Sulfoxide → HCID 87822476, compound

To a flame-dried flask was added oxalyl chloride (70 μL) followed by the addition of dry CH2Cl2 (2 mL). The resulting colorless solution was brought to −63° C. (dry ice/CHCl3) and a solution of DMSO (70 μL) in 0.5 mL dry CH2Cl2 was slowly added drop wise. The (tert-butoxy)-N-[(6-bromo(2-pyridyl))methyl]-N-[2-hydroxy-1-(methylethyl)ethyl]carboxamide (0.19 g, 0.51 mmol), previously dissolved in dry CH2Cl2 (2 mL), was added slowly dropwise. The resulting mixture was kept at −63° C., and stirred for 30 min followed by the slowly addition of a solution of TEA (0.3 mL) in dry CH2Cl2 (1 mL). The mixture was stirred at −63° C. until all the starting material was consumed (checked by MS)(1.5 h). The mixture was brought to −20° C., quenched with a saturated solution of NH4Cl (15 mL) and diluted with EtOAc (35 mL). The organic phase was separated and the aqueous phase was extracted with EtOAc (3×30 mL). The organic layers were combined, dried over MgSO4, filtered and concentrated by rotary evaporation without further purification to afford the title compound as a yellow-semi solid. EI-MS m/z 371 (M+H).

1. customwas brought to −63° C.
2. additionwas added slowly dropwise
3. customwas kept at −63° C.
4. stirringThe mixture was stirred at −63° C. until all the starting material
5. customwas consumed (checked by MS)(1.5 h)
6. customwas brought to −20° C.
7. customquenched with a saturated solution of NH4Cl (15 mL)
8. additiondiluted with EtOAc (35 mL)
9. customThe organic phase was separated
10. extractionthe aqueous phase was extracted with EtOAc (3×30 mL)
11. dry with materialdried over MgSO4
12. filtrationfiltered
13. concentrationconcentrated by rotary evaporation without further purification

ORD record

ord-c226926615614cd8acedec433574f631

Source dataset

uspto-grants-2007_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07196104B2