Trifluoroacetic acid → HCID 11816794, compound

HRID 853049Notes

Reaction equation

HRID 853049 reaction equation
[CH3:1][CH2:2][O:3][C:4]([C:6]1[N:7](C(OC(C)(C)C)=O)[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:15][CH3:16])=[O:5].FC(F)(F)C(O)=O>ClCCl>[CH2:2]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:15][CH3:16])=[O:5])[CH3:1]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 11392958HCID 11392958, compound

Product 1

HCID 11816794HCID 11816794, compoundYield 76.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

7-Ethyl-indole-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester (76.6 g, 0.24 mol was dissolved in 450 mL dichloromethane and cooled to 0° C. Trifluoroacetic acid (150.0 mL, 1.96 mol) was added within 30 min. and after an additional 45 min. the reaction mixture was concentrated at a rotary evaporator. The residue was dissolved in 300 mL dichloromethane and poured cautiously onto 500 mL saturated aq. sodium bicarbonate solution. The phases were separated and the aqueous phase was extracted twice with dichloromethane. The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated on a rotary evaporator. The residue was suspended in 400 mL n-hexane and put in an ultrasonic bath for 15 min. The suspension was filtered and the filter cake was washed with 100 mL n-hexane. This procedure was repeated to give the desired product as a light brown solid (40.2 g, 76.6%). EI-MS: m/e=217.1 ([M])

Workup

  1. concentrationwas concentrated at a rotary evaporator
  2. dissolutionThe residue was dissolved in 300 mL dichloromethane
  3. additionpoured cautiously onto 500 mL saturated aq. sodium bicarbonate solution
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted twice with dichloromethane
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated on a rotary evaporator
  10. filtrationThe suspension was filtered
  11. washthe filter cake was washed with 100 mL n-hexane

Sources & evidence

ORD record
ord-2bbfe52d7e374a1196114958408c5a4b
Source dataset
uspto-grants-2007_08
Patent number
US07253281B2

Reaction notes

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