Potassium Carbonate → HCID 89700053, compound

HRID 1055653Notes

Reaction equation

HRID 1055653 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:11]([F:16])([F:15])([F:14])([F:13])[F:12])[CH:10]=1)[C:5]([OH:7])=[O:6].[CH3:17][S:18]([O-:20])=[O:19].[Na+].N1CCC[C@H]1C(O)=O.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.O.[Cu]I>[CH3:17][S:18]([C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:11]([F:16])([F:15])([F:14])([F:13])[F:12])[CH:10]=1)[C:5]([OH:7])=[O:6])(=[O:20])=[O:19]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 145742L-ProlineHCID 2733271Sodium methanesulfinateHCID 58137421HCID 58137421, compound

Product 1

HCID 89700053HCID 89700053, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 23503278(Methanesulfinyl)methane--water (1/1)Solvent

Conditions

Temperature
150 °C

Procedure

A mixture of 250 mg (0.764 mmol) of the compound of Example 15A, 86 mg (0.841 mmol) of sodium methanesulphinate, 19 mg (0.168 mmol) of (S)-proline and 23 mg (0.168 mmol) of potassium carbonate in 3 ml of DMSO/water (4:1) was initially degassed, 16 mg (0.084 mmol) of copper(I) iodide were then added and the mixture was finally, under an argon atmosphere, heated in a microwave oven (Biotage Initiator, with Dynamic Field Tuning) at 150° C. for 30 min. After cooling to RT, the reaction mixture was filtered through a little Celite and then separated into its components by preparative HPLC (Method 9). Concentration of the product fractions and drying of the residue under high vacuum gave 83 mg (33% of theory) of the title compound.

Workup

  1. customwas initially degassed
  2. temperatureAfter cooling to RT
  3. filtrationthe reaction mixture was filtered through a little Celite
  4. customseparated into its components by preparative HPLC (Method 9)
  5. customConcentration of the product fractions and drying of the residue under high vacuum

Sources & evidence

ORD record
ord-8335169370844317815f721819a81b90
Source dataset
uspto-grants-2016_07
Patent number
US09394309B2

Reaction notes

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