Sodium Sulfite → HCID 90449956, compound

HRID 1411256Notes

Reaction equation

HRID 1411256 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:14][CH2:13][N:12]([C:15]([O:17][CH3:18])=[O:16])[CH2:11]3)[CH2:9][N:8]([C:19](=[O:28])[NH:20][C:21]3[S:22][C:23](SC)=[CH:24][N:25]=3)[C:5]2=[CH:6][CH:7]=1.Cl[C:30]1C=CC=C(C(OO)=O)C=1.[S:40]([O-:43])([O-])=[O:41].[Na+].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:14][CH2:13][N:12]([C:15]([O:17][CH3:18])=[O:16])[CH2:11]3)[CH2:9][N:8]([C:19](=[O:28])[NH:20][C:21]3[S:22][C:23]([S:40]([CH3:30])(=[O:43])=[O:41])=[CH:24][N:25]=3)[C:5]2=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 89520614HCID 89520614, compound

Product 1

HCID 90449956HCID 90449956, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The methyl 5-chloro-1-((5-(methylthio)thiazol-2-yl)carbamoyl)spiro[indoline-3,3′-pyrrolidine]-1′-carboxylate (41.0 mg, 0.093 mmol) obtained in Example 127 was dissolved in methylene chloride (4 mL). Thereafter, meta-chloroperbenzoic acid (64.0 mg, 0.37 mmol) was added to the above obtained solution, and the thus obtained mixture was then stirred at room temperature for 2 hours. Thereafter, the reaction solution was diluted with an aqueous solution of sodium sulfite, and was then extracted with chloroform. The organic layer was washed with brine, and was then dried over anhydrous sodium sulfate, followed by concentration in vacuo. The obtained residue was purified by silica gel column chromatography (chloroform:methanol=10:1) to obtain the captioned compound (22.0 mg, 50%) in the form of a white solid.

Workup

  1. extractionwas then extracted with chloroform
  2. washThe organic layer was washed with brine
  3. dry with materialwas then dried over anhydrous sodium sulfate
  4. concentrationfollowed by concentration in vacuo
  5. customThe obtained residue was purified by silica gel column chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-ab483b6ea5cd411faeda93ec880f7719
Source dataset
uspto-grants-2014_12
Patent number
US08921576B2

Reaction notes

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