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

HRID 2359449Notes

Reaction equation

HRID 2359449 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.CCN(C(C)C)C(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-ylcarbamate (3.0 g, 13.4 mmol) and DIPEA (5.0 g, 40 mmol) in acetonitrile (30 mL) was added MsCl (2.0 g, 17.4 mmol) over a period of 30 min at 0° C. and the mixture was stirred for 2 h at room temperature. The reaction was quenched by adding saturated aqueous NaHCO3 and extracted with ethyl acetate (3×60 mL). The combined organic layers were washed with brine, dried (Na2SO4) and concentrated under reduced pressure to afford essentially quantitative yield of crude (6-(tert-butoxycarbonylamino)pyridin-2-yl)methyl methanesulfonate.

Workup

  1. customThe reaction was quenched
  2. additionby adding saturated aqueous NaHCO3
  3. extractionextracted with ethyl acetate (3×60 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-84cc8217c730444386c7bcf15972ee86
Source dataset
uspto-grants-2014_04
Patent number
US08685970B2

Reaction notes

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