p-Toluenesulfonic acid monohydrate → HCID 68227582, compound

HRID 1400137Notes

Reaction equation

HRID 1400137 reaction equation
[O:1]=[C:2]1[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12]3([C:16]([OH:18])=[O:17])[CH2:15][CH2:14][CH2:13]3)[CH:8]=2)[NH:3]1.O.[C:20]1(C)C=CC(S(O)(=O)=O)=C[CH:21]=1>C(O)C>[O:1]=[C:2]1[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12]3([C:16]([O:18][CH2:20][CH3:21])=[O:17])[CH2:13][CH2:14][CH2:15]3)[CH:8]=2)[NH:3]1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 67154055HCID 67154055, compound

Product 1

HCID 68227582HCID 68227582, compoundYield 334.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

7.2 g of 1-(2,3-dioxoindolin-5-yl)cyclobutanecarboxylic acid are dissolved in 100 ml of ethanol, and 500 mg of toluene-4-sulfonic acid monohydrate are added. The mixture is heated at 80° C. for 1 h and subsequently evaporated in vacuo. The residue is taken up in 100 ml of water and 100 ml of ethyl acetate, and the aqueous phase is separated off. The aqueous phase is washed a further twice with 100 ml of ethyl acetate each time. The combined organic phases are dried over sodium sulfate, filtered and evaporated to dryness in vacuo. The residue is purified by column chromatography (reversed phase), giving 2.4 g (30%) of ethyl 1-(2,3-dioxoindolin-5-yl)cyclobutanecarboxylate;

Workup

  1. customsubsequently evaporated in vacuo
  2. custom100 ml of ethyl acetate, and the aqueous phase is separated off
  3. washThe aqueous phase is washed a further twice with 100 ml of ethyl acetate each time
  4. dry with materialThe combined organic phases are dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness in vacuo
  7. customThe residue is purified by column chromatography (reversed phase)

Sources & evidence

ORD record
ord-1fcbadc8951442deb4b20c87c9ef54f1
Source dataset
uspto-grants-2014_12
Patent number
US08906930B2

Reaction notes

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