HCID 10178261, compound → HCID 18172597, compound

HRID 397203Notes

Reaction equation

HRID 397203 reaction equation
[CH:1]1([S:6][CH:7]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=2)[C:8]([NH:10][C:11]2[S:12][CH:13]=[CH:14][N:15]=2)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.I([O-])(=O)(=O)=[O:25].[Na+]>CO.O>[CH:1]1([S:6]([CH:7]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=2)[C:8]([NH:10][C:11]2[S:12][CH:13]=[CH:14][N:15]=2)=[O:9])=[O:25])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 10178261HCID 10178261, compoundHCID 23667635Sodium periodate

Product 1

HCID 18172597HCID 18172597, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of rac-2-cyclopentylsulfanyl-2-(3,4-dichloro-phenyl)-N-thiazol-2-yl-acetamide (Example 10; 34 mg, 0.088 mmol) in methanol (2 mL) was added a solution of sodium periodate (34 mg, 0.16 mmol) in water (1 mL) and the mixture was stirred at 25° C. After 6 h, the precipitate was filtered off and washed with dichloromethane (15 mL). The organic layer was set aside and the aqueous layer was extracted with dichloromethane (3×10 mL). The combined organic layers were dried over sodium sulfate, filtered and evaporated under reduced pressure. Chromatography of the residue (Biotage Flash 12M column, 50/50 hexanes/ethyl acetate) afforded rac-2-cyclopentanesulfinyl-2-(3,4-dichloro-phenyl)-N-thiazol-2-yl-acetamide (23 mg, 66% yield) as a colorless oil: EI-HRMS m/e calculated for C16H16N2O2S2Cl2 (M+) 402.0030, found 402.0035.

Workup

  1. filtrationthe precipitate was filtered off
  2. washwashed with dichloromethane (15 mL)
  3. extractionthe aqueous layer was extracted with dichloromethane (3×10 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-cdac152b51054d72a83ba65c12cee550
Source dataset
uspto-grants-2003_08
Patent number
US06608218B2

Reaction notes

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