Sodium periodate → HCID 44218659, compound

HRID 39225

Reaction equation

HRID 39225 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10]([N:13]2[CH2:17][CH2:16][S:15][CH2:14]2)(=[O:12])=[O:11])[C:3]=1[C:4]#[N:5].I([O-])(=O)(=O)=[O:19].[Na+]>CO.O>[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10]([N:13]2[CH2:17][CH2:16][S:15](=[O:19])[CH2:14]2)(=[O:12])=[O:11])[C:3]=1[C:4]#[N:5]

Participants

5

Reactant 2

HCID 23667635Sodium periodateHCID 442186552-Fluoro-6-(thiazolidine-3-sulfonyl)-benzonitrile

Product 1

HCID 44218659HCID 44218659, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

54 mg of 2-Fluoro-6-(thiazolidine-3-sulfonyl)-benzonitrile in 10 ml of methanol and 1 ml of water are treated with 45 mg of sodium periodate, and the mixture is stirred for 14 hours at room temperature. The reaction mixture is poured into water, and the aqueous layer is extracted three times with ethyl acetate. The combined organic layers are dried over sodium sulfate, filtered and concentrated in vacuo. Purification by reverse phase HPLC affords 40 mg of 2-Fluoro-6-(1-oxo-1 lambda*4*-thiazolidine-3-sulfonyl)-benzonitrile.

Workup

  1. extractionthe aqueous layer is extracted three times with ethyl acetate
  2. dry with materialThe combined organic layers are dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification by reverse phase HPLC

Sources & evidence

ORD record
ord-fd5234d09edb41feb82f3dd1a0012650
Source dataset
uspto-grants-2013_09
Patent number
US08524896B2

Linked notes

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