Triethylamine → (6-(Tert-butoxycarbonylamino)pyridin-3-yl)methyl methanesulfonate
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
Product 1
Reagents, catalysts & solvents 3
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
- extractionextracted with EtOAc
- washThe organic phase was washed with H2O and brine
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-1bc7ee17841f477e9d6844ea87cf2092
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08536175B2
Reaction notes
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