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

HRID 2409627Notes

Reaction equation

HRID 2409627 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-72f8dede0dae4d31ab5d9baa87815a09
Source dataset
uspto-grants-2014_08
Patent number
US08815901B2

Reaction notes

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