Dimethyl Sulfoxide → HCID 59021633, compound

To a stirred solution of 36 ml oxalyl chloride (0.42 mol; Fluka) in 1100 ml dichloromethane were added at −70° C. a solution of 44 ml dimethyl sulfoxide (0.62 mol) in 800 ml dichloromethane over 0.5 h. After stirring at −700 for 15 min a solution of 77.5 g N-benzyl-N-methyl-isoleucinol (0.35 mol) in 700 ml dichloromethane was added at −70° C. over ˜0.5 h and stirring was continued for 15 min. After the addition of 234 ml triethylamine (1.68 mol) at −65° C. stirring was continued for 5 min and the white suspension stirred at −50° C. for 1 h. The dry ice-bath was removed and 3000 ml deionized water was added drop wise and under stirring while the reaction mixture was warmed up to RT. The organic layer was washed twice with 2000 ml 10% brine and the organic layer was dried (Na2SO4). Removal of the solvent by rotary evaporation (40° C./≧10 mbar/0.1 mbar, 2 h) yielded 76.9 g (100.2%) yellow oily product which was used without purification in the next step.

1. additionwas added at −70° C. over ˜0.5 h
2. stirringstirring
3. waitwas continued for 5 min
4. stirringthe white suspension stirred at −50° C. for 1 h
5. customThe dry ice-bath was removed
6. additionwas added drop wise
7. stirringunder stirring while the reaction mixture
8. washThe organic layer was washed twice with 2000 ml 10% brine
9. dry with materialthe organic layer was dried (Na2SO4)
10. customRemoval of the solvent
11. customby rotary evaporation (40° C./≧10 mbar/0.1 mbar, 2 h)

ORD record

ord-f7a16f48105e48c88fda015c3548724a

Source dataset

uspto-grants-2007_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07312343B2