Methanesulfonyl chloride → (6-(Tert-butoxycarbonylamino)pyridin-3-yl)methyl methanesulfonate

HRID 85155Notes

Reaction equation

HRID 85155 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[N:7][CH:8]=1.CCN(C(C)C)C(C)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>C1COCC1>[CH3:26][S:27]([O:1][CH2:2][C:3]1[CH:8]=[N:7][C:6]([NH:9][C:10]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:16])=[CH:5][CH:4]=1)(=[O:29])=[O:28]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 3575389tert-Butyl 5-(hydroxymethyl)pyridin-2-ylcarbamate

Product 1

HCID 86641141(6-(Tert-butoxycarbonylamino)pyridin-3-yl)methyl methanesulfonateYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture containing tert-butyl 5-(hydroxymethyl)pyridin-2-ylcarbamate (101; 4.5 g, 20.2 mmol) and DIPEA (16.0 g, 121 mmol) in THF (45 mL) was added MsCl (6.93 g, 60.5 mmol) over a period of 30 min at 0° C. The resulting reaction mixture was stirred at room temperature for 12 h. The mixture was then washed with water (2×5 mL), dried (Na2SO4) and concentrated under reduced pressure. The resulting residue was purified by chromatography (10:1 petroleum ether/ethyl acetate) to afford (6-(tert-butoxycarbonylamino)pyridin-3-yl)methyl methanesulfonate 102 (3.0 g, 61%).

Workup

  1. customThe resulting reaction mixture
  2. washThe mixture was then washed with water (2×5 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by chromatography (10:1 petroleum ether/ethyl acetate)

Sources & evidence

ORD record
ord-22bb44f2755c42419a03a030577c19ee
Source dataset
uspto-grants-2014_09
Patent number
US08846947B2

Reaction notes

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