Hydrogen Peroxide → HCID 59278114, compound
Reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([C@@H:9]([NH:12][S:13]([C:15]([CH3:18])([CH3:17])[CH3:16])=[O:14])[CH2:10][CH3:11])[CH:6]=[CH:5][N:4]=1)#[N:2].C(=O)([O-])[O-:20].[K+].[K+].OO>CS(C)=O.C(OCC)(=O)C>[CH3:18][C:15]([S:13]([NH:12][C@H:9]([C:7]1[CH:6]=[CH:5][N:4]=[C:3]([C:1]([NH2:2])=[O:20])[CH:8]=1)[CH2:10][CH3:11])=[O:14])([CH3:17])[CH3:16]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 5 °C
Procedure
To a rapidly stirred solution of 2-Methyl-propane-2-sulfinic acid [(S)-1-(2-cyano-pyridin-4-yl)-propyl]-amide (4.40 g, 16.6 mmol) in DMSO (70 mL) at 10° C. was added potassium carbonate (3.00 g, 21.7 mmol) portionwise and hydrogen peroxide (30 wt. % in water, 6.16 mL, 54.4 mmol) dropwise. The reaction was stirred at room temp. for 3.5 h. The reaction was cooled to 5° C., diluted with ethyl acetate (100 mL) and quenched with sodium thiosulfate solution (10% in water, 25 mL), stirred at 5° C. for 1 h. The organic phase was separated, the aqueous phase was extracted with ethyl acetate (4×100 mL), the combined organic extracts were washed with water (3×50 mL), brine, dried over sodium sulfate, filtered and concentrated to give 4-[(S)-1-(2-Methyl-propane-2-sulfinylamino)-propyl]-pyridine-2-carboxylic acid amide (5.50 g, 99%) as a thick oil.
Workup
- customquenched with sodium thiosulfate solution (10% in water, 25 mL)
- stirringstirred at 5° C. for 1 h
- customThe organic phase was separated
- extractionthe aqueous phase was extracted with ethyl acetate (4×100 mL)
- washthe combined organic extracts were washed with water (3×50 mL), brine
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-5f3f9afed49e4262b3a4bee7399c7a14
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08293917B2
Reaction notes
Loading…