Pyridine → 2-(2-Azidoethoxy)ethyl 4-methylbenzenesulfonate

HRID 1521924Notes

Reaction equation

HRID 1521924 reaction equation
[N:1]([CH2:4][CH2:5][O:6][CH2:7][CH2:8][OH:9])=[N+:2]=[N-:3].N1C=CC=CC=1.[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[N:1]([CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][S:22]([C:19]1[CH:20]=[CH:21][C:16]([CH3:26])=[CH:17][CH:18]=1)(=[O:24])=[O:23])=[N+:2]=[N-:3]

Participants

6

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 114007892-(2-Azidoethoxy)ethan-1-ol

Product 1

HCID 600204482-(2-Azidoethoxy)ethyl 4-methylbenzenesulfonateYield 78%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(2-azido-ethoxy)-ethanol 2 (14.1 g, 0.108 mol) and pyridine (13 ml, 1.5 equiv.) in CH2Cl2 (150 ml) was cooled in an ice bath. p-Toluenesulfonyl chloride (30.7 g, 1.5 equiv.) then DMAP (173 mg, 0.01 equiv.) were added. The reaction mixture was stirred at RT for 72 h, then washed with a 1 M HCl aqueous solution (3×50 ml), dried over MgSO4, filtrated then concentrated under reduced pressure. Purification by flash column chromatography (eluent: pet. ether/AcOEt 9:1 then 7:3) afforded tosylate 3 as a colorless oil (23.8 g, 78%). 1H and 13C NMR spectra matched the literature data (Gill, H. et al. J. Med. Chem. 2009, 52, 5816-5825).

Workup

  1. washwashed with a 1 M HCl aqueous solution (3×50 ml)
  2. dry with materialdried over MgSO4
  3. filtrationfiltrated
  4. concentrationthen concentrated under reduced pressure
  5. customPurification by flash column chromatography (eluent

Sources & evidence

ORD record
ord-e150d43efa3d45daa39d92a2f436d667
Source dataset
uspto-grants-2015_07
Patent number
US09073969B2

Reaction notes

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