Dimethylformamide → HCID 178473095, compound

HRID 1634301Notes

Reaction equation

HRID 1634301 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:22])[C:7]([OH:21])=[CH:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([Cl:20])[CH:18]=2)[NH:13][CH:12]=1)=[O:10])[CH3:4].[C:23]1([S:29](Cl)(=[O:31])=[O:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.CN(C=O)C>C1COCC1>[CH2:3]([O:5][C:6](=[O:22])[C:7]([OH:21])=[CH:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([Cl:20])[CH:18]=2)[N:13]([S:29]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)(=[O:31])=[O:30])[CH:12]=1)=[O:10])[CH3:4]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 178473094HCID 178473094, compound

Product 1

HCID 178473095HCID 178473095, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 0.88 g (22 mmol) of sodium hydride (60% dispersion in mineral oil) in THF (50 ml) was added under ice-cooling, 2.94 g (10 mmol) of 4-(5-chloroindol-3-yl)-2-hydroxy-4-oxo-2-butenoic acid ethyl ester prepared in Example 1 (1). After stirring for 15 min at room temperature, to the mixture was added dropwise a solution of 2.12 g (12 mmol) of benzenesulfonyl chloride in THF (20 ml). After stirring for 2 hours at room temperature, to the mixture was added DMF (8 ml). After stirring for additional 30 min, the reaction mixture was poured into ice-water containing 1N hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and then dried. The solvent was concentrated and the residue was crystallized from ether to give crude crystal, which was washed with ether to give 3.75 g of the titled compound. Yield: 87%. Subsequent recrystallization from ethyl acetate afforded the pure ester, melted at. 156-157° C.

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. stirringAfter stirring for 2 hours at room temperature, to the mixture
  4. stirringAfter stirring for additional 30 min
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with water and saturated brine
  7. customdried
  8. concentrationThe solvent was concentrated
  9. customthe residue was crystallized from ether
  10. customto give crude crystal, which
  11. washwas washed with ether

Sources & evidence

ORD record
ord-4f155dba6ffb47cd83fd9464e760d857
Source dataset
uspto-grants-2003_01
Patent number
US06506787B2

Reaction notes

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