Methanesulfonyl chloride → HCID 178441166, compound
Reaction equation
[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11](=[O:22])[C:12]([CH3:21])([S:14][CH2:15][CH:16]2[CH2:20][CH2:19][NH:18][CH2:17]2)[CH3:13])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C.[CH3:32][S:33](Cl)(=[O:35])=[O:34]>C1COCC1>[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11](=[O:22])[C:12]([SH:14]([CH2:15][CH:16]2[CH2:20][CH2:19][NH:18][CH2:17]2)[S:33]([CH3:32])(=[O:35])=[O:34])([CH3:13])[CH3:21])[CH:6]=1)([CH3:2])([CH3:3])[CH3:4]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
To a solution of 172 mg (0.52 mmol) of N-(5-tert-butyl-isoxazol-3-yl)-2-methyl-2-(pyrrolidin-3-ylmethylsulfanyl)-propionamide (prepared according to Method I, step 1) and 0.18 mL (1.04 mmol) of N,N-diisopropylethylamine in THF were added 0.16 mL (2.11 mmol) of methanesulfonyl chloride. The reaction was heated within a microwave to 90° C. for 0.5 h. The mixture was concentrated under reduced pressure. The residue was dissolved in DCM (5 mL) and washed with saturated aqueous NaHCO3 solution (5 mL). The organic layer was dried over Na2SO4, filtered and the filtrate was concentrated under reduced pressure to afford 168 mg of N-(5-tert-butyl-isoxazol-3-yl)-2-(1-methanesulfonyl-pyrrolidin-3-ylmethylsulfanyl)-2-methyl-propionamide, which was used in the next step without further purification.
Workup
- concentrationThe mixture was concentrated under reduced pressure
- dissolutionThe residue was dissolved in DCM (5 mL)
- washwashed with saturated aqueous NaHCO3 solution (5 mL)
- dry with materialThe organic layer was dried over Na2SO4
- filtrationfiltered
- concentrationthe filtrate was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-2a2529c63b77412a91e1cd95f8ee4bd0
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08829034B2
Reaction notes
Loading…