Pyridine → HCID 86622573, compound

HRID 2097348Notes

Reaction equation

HRID 2097348 reaction equation
[S:1](Cl)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].N1C=CC=CC=1.[N:18]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][OH:28])=[N+:19]=[N-:20]>C(Cl)Cl.CCOC(C)=O>[N:18]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28][S:1]([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2])=[N+:19]=[N-:20]

Participants

6

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 231324227-Azido-1-heptanol

Product 1

HCID 86622573HCID 86622573, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a731fec637cb49d593ff04a9e5f213e5
Source dataset
uspto-grants-2013_05
Patent number
US08450348B2

Reaction notes

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