Sodium methanesulfinate → HCID 66727370, compound

HRID 1423047Notes

Reaction equation

HRID 1423047 reaction equation
Br[C:2]1[CH:7]=[C:6]([C@H:8]([NH:11][S:12]([C:14]([CH3:17])([CH3:16])[CH3:15])=[O:13])[CH2:9][CH3:10])[CH:5]=[CH:4][N:3]=1.[CH3:18][S:19]([O-:21])=[O:20].[Na+]>CS(C)=O.[NH4+].[Cl-].C([O-])(O)=O.[Na+].CCOC(C)=O.[Cu]I>[CH3:18][S:19]([C:2]1[CH:7]=[C:6]([C@@H:8]([NH:11][S:12]([C:14]([CH3:17])([CH3:16])[CH3:15])=[O:13])[CH2:9][CH3:10])[CH:5]=[CH:4][N:3]=1)(=[O:21])=[O:20]

Participants

8

Reactant 2

HCID 2733271Sodium methanesulfinateHCID 86640805HCID 86640805, compound

Product 1

HCID 66727370HCID 66727370, compound

Reagents, catalysts & solvents 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of 2-methyl-propane-2-sulfinic acid [(R)-1-(2-bromopyridin-4-yl)-propyl]-amide (6.00 g, 18.8 mmol) in DMSO (240 mL) is added sodium methanesulfinate (6.77 g, 56.4 mmol) and copper (I) iodide (10.7 g, 56.4 mmol). The mixture is then heated at 130° C. for 45 minutes. The reaction is diluted with saturated aqueous NH4Cl (90 mL), saturated NaHCO3 (10 mL), and EtOAc (150 mL), and sonicated for 10 minutes to dissolve all the solids. The phases are separated and the organic layer is washed with a 9:1 mixture of saturated NH4Cl-saturated NaHCO3 (100 mL). The combined aqueous phases are extracted with EtOAc (150 mL). Combined organic layers are washed with brine, dried over sodium sulfate, filtered and concentrated. The crude material is purified by silica gel chromatography eluting with a gradient of 0-100% EtOAc in hexanes to afford 2-methyl-propane-2-sulfinic acid [(S)-1-(2-methanesulfonyl-pyridin-4-yl)-propyl]-amide as an oil.

Workup

  1. customsonicated for 10 minutes
  2. dissolutionto dissolve all the solids
  3. customThe phases are separated
  4. washthe organic layer is washed with a 9:1 mixture of saturated NH4Cl-saturated NaHCO3 (100 mL)
  5. extractionThe combined aqueous phases are extracted with EtOAc (150 mL)
  6. washCombined organic layers are washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude material is purified by silica gel chromatography
  11. washeluting with a gradient of 0-100% EtOAc in hexanes

Sources & evidence

ORD record
ord-d64c4e497d694636bfc952781682c9de
Source dataset
uspto-grants-2015_01
Patent number
US08927550B2

Reaction notes

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