HCID 10366670, compound → HCID 10096248, compound

HRID 719865Notes

Reaction equation

HRID 719865 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:12]([CH2:24][CH:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)[C:13]([NH:15][C:16]2[CH:21]=[N:20][C:19]([S:22][CH3:23])=[CH:18][N:17]=2)=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].[Na].I([O-])(=O)(=O)=[O:32]>O1CCCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:12]([CH2:24][CH:25]2[CH2:26][CH2:27][CH2:28][CH2:29]2)[C:13]([NH:15][C:16]2[CH:21]=[N:20][C:19]([S:22]([CH3:23])=[O:32])=[CH:18][N:17]=2)=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9]

Participants

5

Reactant 2

HCID 10366670HCID 10366670, compoundHCID 86593780HCID 86593780, compound

Product 1

HCID 10096248HCID 10096248, compoundYield 46.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-(5-methylsulfanyl-pyrazin-2-yl)-propionamide (prepared as in Example 4, 0.20 g, 0.441 mmol) in tetrahydrofuran (3 mL) was added dropwise to a solution of sodium-meta-periodate (0.189 g, 0.882 mmol) in water (1.5 mL). The resulting reaction mixture was stirred at 25° C. for 72 h. The reaction mixture was then concentrated in vacuo, and the residue was then diluted with chloroform (25 mL). The organic layer was washed with water (25 mL), dried over magnesium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40S, Silica, 2/1 ethyl acetate/hexanes) afforded 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-(5-methane-sulfinyl-pyrazin-2-yl)-propionamide (96 mg, 46%) as a white foam: mp 88–95° C. (foam to gel); (ES)+-HRMS m/e calcd for C20H24ClN3O4S2 (M+H)+ 470.0970 found 470.0976.

Workup

  1. customThe resulting reaction mixture
  2. concentrationThe reaction mixture was then concentrated in vacuo
  3. additionthe residue was then diluted with chloroform (25 mL)
  4. washThe organic layer was washed with water (25 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1c07a2b231c64ae1975bdd3b6b10a914
Source dataset
uspto-grants-2006_11
Patent number
US07132425B2

Reaction notes

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