Pyridine → 2-[2-(2-Azido-Ethoxy)-Ethylsulfonyl]-Ethyl 4-Nitrophenyl Carbonate

HRID 1521927Notes

Reaction equation

HRID 1521927 reaction equation
[N:1]([CH2:4][CH2:5][O:6][CH2:7][CH2:8][S:9]([CH2:12][CH2:13][OH:14])(=[O:11])=[O:10])=[N+:2]=[N-:3].N1C=CC=CC=1.Cl[C:22]([O:24][C:25]1[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=1)=[O:23]>C(Cl)Cl>[C:22](=[O:23])([O:24][C:25]1[CH:26]=[CH:27][C:28]([N+:31]([O-:33])=[O:32])=[CH:29][CH:30]=1)[O:14][CH2:13][CH2:12][S:9]([CH2:8][CH2:7][O:6][CH2:5][CH2:4][N:1]=[N+:2]=[N-:3])(=[O:11])=[O:10]

Participants

5

Reactant 3

HCID 1049PyridineHCID 821294-Nitrophenyl chloroformateHCID 866703002-[2-(2-Azido-Ethoxy)-Ethylsulfonyl]-Ethanol

Product 1

HCID 529360022-[2-(2-Azido-Ethoxy)-Ethylsulfonyl]-Ethyl 4-Nitrophenyl CarbonateYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of alcohol 5 (4.0 g, 17.9 mmol) and pyridine (10 ml, 6.9 equiv.) in CH2Cl2 (100 ml) was cooled in an ice bath and p-nitrophenyl chloroformate (5.42 g, 1.5 equiv.) was added. The resulting solution was stirred at RT for 16 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 7:3 then 1:1) afforded carbonate 6 as a white amorphous solid (6.3 g, 91%).

Workup

  1. washthen washed 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-9c6d5f4cb9534c2b8631f8c173355347
Source dataset
uspto-grants-2015_07
Patent number
US09073969B2

Reaction notes

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