Potassium Carbonate → Methyl 5-(2-(4-chlorobenzenesulphonylamino)indan-5-yl)-5-(3-pyridyl)pent-4-enoate

HRID 1490374Notes

Reaction equation

HRID 1490374 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH:12]2[CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:21]([C:28]4[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=4)=[CH:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26])[CH:18]=3)[CH2:13]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:34](=O)([O-])[O-].[K+].[K+]>CO.Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH:12]2[CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:21]([C:28]4[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=4)=[CH:22][CH2:23][CH2:24][C:25]([O:27][CH3:34])=[O:26])[CH:18]=3)[CH2:13]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 541157275-(2-(4-Chlorobenzenesulphonylamino)indan-5-yl)-5-(3-pyridyl)pent-4-enoic acid

Product 1

HCID 53820407Methyl 5-(2-(4-chlorobenzenesulphonylamino)indan-5-yl)-5-(3-pyridyl)pent-4-enoate

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

3.7 g of 5-(2-(4-chlorobenzenesulphonylamino)indan-5-yl)-5-(3-pyridyl)pent-4-enoic acid are dissolved in 30 ml of methanol into which dry hydrogen chloride is introduced. The solution is stirred overnight and then rotary evaporated. Whilst cooling with ice, the base is liberated with aqueous potassium carbonate solution and then extracted with methylene chloride. The solution is rotary evaporated and the residue is chromatographed over a silica gel column.

Workup

  1. additionis introduced
  2. temperatureWhilst cooling with ice
  3. extractionextracted with methylene chloride
  4. customThe solution is rotary evaporated
  5. customthe residue is chromatographed over a silica gel column

Sources & evidence

ORD record
ord-6e72831112034b8fa64fb67e66779a83
Source dataset
uspto-grants-1997_10
Patent number
US05681961

Reaction notes

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