Ethyl Acetate → HCID 22337089, compound

HRID 585521Notes

Reaction equation

HRID 585521 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[Cl:23][C:24]1[S:28][C:27]([C:29]([NH:31][C:32]2[CH:40]=[CH:39][CH:38]=[C:37]3[C:33]=2[CH2:34][N:35]([CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[C:45]([CH2:49][OH:50])[CH:44]=2)[C:36]3=[O:41])=[O:30])=[CH:26][CH:25]=1.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>ClCCl.N1C=CC=CC=1>[Cl:23][C:24]1[S:28][C:27]([C:29]([NH:31][C:32]2[CH:40]=[CH:39][CH:38]=[C:37]3[C:33]=2[CH2:34][N:35]([CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[C:45]([CH:49]=[O:50])[CH:44]=2)[C:36]3=[O:41])=[O:30])=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 22337086HCID 22337086, compound

Product 1

HCID 22337089HCID 22337089, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

Dess-Martin periodinane (1.9 g, 4.6 mmol) is added to a solution of 5-chloro-N-{2-[3-(hydroxymethyl)benzyl]-1-oxo-2,3-dihydro-1H-isoindol-4-yl}-2-thiophenecarboxamide (1.6 g, 3.8 mmol) in dichloromethane (38 ml) and pyridine (1.5 ml) and the mixture is stirred at room temperature for 6 h, and saturated aqueous sodium bicarbonate solution is then added. After addition of ethyl acetate and phase separation, the aqueous phase is extracted with ethyl acetate. The combined organic phases are dried (sodium sulfate), filtered and concentrated under reduced pressure. The desired product is purified by flash chromatography (dichloromethane/methanol mixtures). Yield: 1.5 g, 97% of theory.

Workup

  1. extractionthe aqueous phase is extracted with ethyl acetate
  2. dry with materialThe combined organic phases are dried (sodium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe desired product is purified by flash chromatography (dichloromethane/methanol mixtures)

Sources & evidence

ORD record
ord-27091271bae64e3b87f5baec30bf222f
Source dataset
uspto-grants-2005_08
Patent number
US06933295B2

Reaction notes

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