Methanesulfonyl chloride → (6-(Tert-butoxycarbonylamino)pyridin-2-yl)methyl methanesulfonate

HRID 1504765Notes

Reaction equation

HRID 1504765 reaction equation
[OH:1][CH2:2][C:3]1[N:8]=[C:7]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:6]=[CH:5][CH:4]=1.C(N(C(C)C)CC)(C)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>C(#N)C>[CH3:26][S:27]([O:1][CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([NH:9][C:10]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:16])[N:8]=1)(=[O:29])=[O:28]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 19349090Tert-butyl (6-(hydroxymethyl)pyridin-2-yl)carbamate

Product 1

HCID 19349110(6-(Tert-butoxycarbonylamino)pyridin-2-yl)methyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of tert-butyl [6-(hydroxymethyl)pyridin-2-yl]carbamate (252 mg, 1.12 mmol) in acetonitrile (2.5 mL) and diisopropylethylamine (0.59 mL, 3.4 mmol) was added methanesulfonyl chloride (0.094 mL, 1.2 mmol) at 0° C. The reaction mixture was warmed to room temperature and stirred for 2 additional hours. The reaction mixture was quenched with saturated aqueous sodium bicarbonate and the mixture was extracted with ethyl acetate (2×). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford {6-[(tert-butoxycarbonyl)amino]pyridin-2-yl}methyl methanesulfonate that was used without further purification. MS ESI calc'd for C12H19N2O5S [M+H]+ 303. found 303.

Workup

  1. customThe reaction mixture was quenched with saturated aqueous sodium bicarbonate
  2. extractionthe mixture was extracted with ethyl acetate (2×)
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0ecd17e49b324065a22bd8e8b0f23bf5
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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