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

HRID 2391780Notes

Reaction equation

HRID 2391780 reaction equation
[CH3:1][S:2]([O:5]S(C)(=O)=O)(=[O:4])=[O:3].[C:10]([O:14][C:15](=[O:25])[NH:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23]O)=[CH:19][N:18]=1)([CH3:13])([CH3:12])[CH3:11].C(N(CC)CC)C>C(Cl)Cl.CCOC(C)=O.O>[C:10]([O:14][C:15]([NH:16][C:17]1[N:18]=[CH:19][C:20]([CH2:23][O:5][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:21][CH:22]=1)=[O:25])([CH3:13])([CH3:12])[CH3:11]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 81560Methanesulfonic anhydrideHCID 3575389tert-Butyl 5-(hydroxymethyl)pyridin-2-ylcarbamate

Product 1

HCID 86641141(6-(Tert-butoxycarbonylamino)pyridin-3-yl)methyl methanesulfonateYield 91.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
5 °C

Procedure

Methanesulfonic anhydride (0.854 g, 4.9 mmol, 1.1 equiv) was added portionwise to a cold (5° C.) mixture of (5-hydroxymethyl-pyridin-2-yl)-carbamic acid tert-butyl ester (Step 26.4) (1 g, 4.5 mmol) and triethylamine (0.75 mL, 5.4 mmol, 1.2 equiv) in DCM (20 mL), under an argon atmosphere. The reaction mixture was allowed to stir for 1 h at 5° C., diluted with EtOAc and H2O, and extracted with EtOAc. The organic phase was washed with H2O and brine, dried (Na2SO4), filtered and concentrated to provide 1.25 g of the title compound as a white solid: tR=2.60 min (System 1).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic phase was washed with H2O and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-29070edf81704d97b562440ed5975c82
Source dataset
uspto-grants-2012_09
Patent number
US08273882B2

Reaction notes

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