Pyridine → HCID 86622573, compound

TsCl (955 mg, 5.0 mmol) and pyridine (435 μL, 5.4 mmol) were added to a solution of 7-azidoheptanol (700 mg, 4.5 mmol) in CH2Cl2 (5 mL). The solution was stirred for 18 h at r.t. The solution was diluted with EtOAc (20 mL) and washed with 5% aqueous KHSO4 solution, sat. aqueous NaHCO3 solution and pH 7 phosphate buffer. The org. layer was concentrated and the residue was treated with water (10 mL) for 4 h to hydrolyse excess TsCl. The mixture was diluted with EtOAc (20 mL), washed with aqueous NaHCO3, dried (Na2SO4), and filtered. Concentration under reduced pressure yielded 7-azidoheptyltosylate (920 mg, 66%). The product was pure enough for further reactions.

1. washwashed with 5% aqueous KHSO4 solution, sat. aqueous NaHCO3 solution and pH 7 phosphate buffer
2. concentrationlayer was concentrated
3. additionthe residue was treated with water (10 mL) for 4 h to hydrolyse excess TsCl
4. additionThe mixture was diluted with EtOAc (20 mL)
5. washwashed with aqueous NaHCO3
6. dry with materialdried (Na2SO4)
7. filtrationfiltered
8. concentrationConcentration under reduced pressure

ORD record

ord-a731fec637cb49d593ff04a9e5f213e5

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08450348B2