Acetic Acid → HCID 178482436, compound

HRID 2227529Notes

Reaction equation

HRID 2227529 reaction equation
[O-]CC.[Na+].[F:5][C:6]([F:24])([F:23])[CH:7]([C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][CH:15]=1)[CH:8]([OH:13])[C:9](OC)=[O:10].Br.[CH3:26][NH:27][C:28](NC)=[NH:29].C(O)(=O)C>C(O)C>[NH:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:14]([CH:7]([CH:8]2[O:13][C:28]([NH:27][CH3:26])=[N:29][C:9]2=[O:10])[C:6]([F:24])([F:23])[F:5])=[CH:15]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 2723922Sodium ethoxideHCID 18473976HCID 18473976, compoundHCID 178419593HCID 178419593, compound

Product 1

HCID 178482436HCID 178482436, compoundYield 20.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium ethoxide (580 mg) was added to a solution of methyl 4,4,4-trifluoro-2-hydroxy-3-(indol-3-yl)butyrate (980 mg) and N,N′-dimethyl guanidine hydrogen bromide (630 mg) in ethanol (2.5 ml). The mixture was refluxed for 1.5 hours and then cooled. To the cooled reaction mixture was added ice water (20 ml). After the pH of the mixture was adjusted to 7 using acetic acid, the whole was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution and then dried over magnesium sulfate. Concentration of the solution under the reduced pressure gave residue, which was subjected to silica gel chromatography. Eluent with ethyl acetate-hexane was collected and concentrated to provide the titled compound (218 mg).

Workup

  1. temperatureThe mixture was refluxed for 1.5 hours
  2. temperaturecooled
  3. customTo the cooled reaction mixture
  4. extractionthe whole was extracted with ethyl acetate
  5. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution
  6. dry with materialdried over magnesium sulfate
  7. customConcentration of the solution under the reduced pressure gave residue, which
  8. customEluent with ethyl acetate-hexane was collected
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-e2fc79b30171413b8fcfc0c880c11224
Source dataset
uspto-grants-2002_07
Patent number
US06414003B1

Reaction notes

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