Sodium Sulfite → HCID 90449435, compound

HRID 1411297Notes

Reaction equation

HRID 1411297 reaction equation
[C:1]([N:4]1[CH2:8][CH2:7][C:6]2([C:16]3[C:11](=[CH:12][CH:13]=[C:14]([CH:17]([OH:19])[CH3:18])[CH:15]=3)[N:10]([C:20]([NH:22][C:23]3[S:24][C:25]([Cl:28])=[CH:26][N:27]=3)=[O:21])[CH2:9]2)[CH2:5]1)(=[O:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[C:1]([N:4]1[CH2:8][CH2:7][C:6]2([C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17](=[O:19])[CH3:18])[CH:15]=3)[N:10]([C:20]([NH:22][C:23]3[S:24][C:25]([Cl:28])=[CH:26][N:27]=3)=[O:21])[CH2:9]2)[CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 159087TriacetoxyperiodinaneHCID 90449833HCID 90449833, compound

Product 1

HCID 90449435HCID 90449435, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The 1′-acetyl-N-(5-chlorothiazol-2-yl)-5-(1-hydroxyethyl)spiro[indoline-3,3′-pyrrolidine]-1-carboxamide (22.3 mg, 0.053 mmol) obtained in Step 2 of Example 401 was dissolved in methylene chloride (0.5 mL). Thereafter, Dess-martin periodinane (27.0 mg, 0.0635 mmol) was added to the above obtained solution at room temperature, and the thus obtained mixture was then stirred at the same temperature as above for 1 hour. Thereafter, an aqueous solution of sodium sulfite was added to the reaction solution, and the mixed solution 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 (21.7 mg, 99%) in the form of a white solid.

Workup

  1. extractionthe mixed solution was 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-ae131e6b4a6d43efb6671d4a67e0fc96
Source dataset
uspto-grants-2014_12
Patent number
US08921576B2

Reaction notes

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