Ethanol → HCID 53653944, compound

HRID 1590708Notes

Reaction equation

HRID 1590708 reaction equation
[C:1]([CH2:4][CH2:5][N:6]1[C:18]2[CH2:17][CH2:16][C@@H:15]([NH:19][S:20]([C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)(=[O:22])=[O:21])[CH2:14][C:13]=2[C:12]2[C:7]1=[CH:8][CH:9]=[CH:10][CH:11]=2)([OH:3])=[O:2].S(=O)(=O)(O)O.C(=O)([O-])O.[Na+].O.[CH2:40](O)[CH3:41]>>[CH2:40]([O:2][C:1]([CH2:4][CH2:5][N:6]1[C:18]2[CH2:17][CH2:16][C@@H:15]([NH:19][S:20]([C:23]3[CH:24]=[CH:25][N:26]=[CH:27][CH:28]=3)(=[O:21])=[O:22])[CH2:14][C:13]=2[C:12]2[C:7]1=[CH:8][CH:9]=[CH:10][CH:11]=2)=[O:3])[CH3:41]

Participants

6

Reactant 5

HCID 702EthanolHCID 962WaterHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 54017881HCID 54017881, compound

Product 1

HCID 53653944HCID 53653944, compound

Procedure

0.9 g (2.3 mmol) of 9-(2-carboxyethyl)-3(R)-(4-pyridylsulphonamido)-1,2,3,4-tetrahydrocarbazole is dissolved in 50 ml of ethanol p.a., 3 ml of concentrated sulphuric acid are added and the mixture is boiled under reflux for 1.5 hours with stirring. After cooling to room temperature, 12.0 g of sodium hydrogen carbonate are added, water is added after the evolution of gas has ended and the mixture is extracted several times with ethyl acetate. The combined organic phases are dried with sodium sulphate and the solvent evaporated therefrom. The crude product is purified by chromatography on silica gel 60 (40-63 μm, Merck, eluant: CH2Cl2 :CH3OH=10:1). Rf =0.63 (CH2Cl2 :CH3OH=10:1)

Workup

  1. temperatureunder reflux for 1.5 hours
  2. extractionthe mixture is extracted several times with ethyl acetate
  3. dry with materialThe combined organic phases are dried with sodium sulphate
  4. customthe solvent evaporated
  5. customThe crude product is purified by chromatography on silica gel 60 (40-63 μm, Merck, eluant: CH2Cl2 :CH3OH=10:1)

Sources & evidence

ORD record
ord-7bcebf46374b43cfbbc98a5f1ae7b846
Source dataset
uspto-grants-1993_04
Patent number
US05204374

Reaction notes

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