Trifluoroacetic acid → HCID 178508208, compound

HRID 1639561Notes

Reaction equation

HRID 1639561 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[S:9]([O:12][C:13]1[CH:29]=[CH:28][C:16]2[NH:17][C:18]([NH:20]C(OC(C)(C)C)=O)=[N:19][C:15]=2[CH:14]=1)(=[O:11])=[O:10].FC(F)(F)C(O)=O>ClCCl.CCCCC>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[S:9]([O:12][C:13]1[CH:29]=[CH:28][C:16]2[NH:17][C:18]([NH2:20])=[N:19][C:15]=2[CH:14]=1)(=[O:11])=[O:10]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 178452972HCID 178452972, compound

Product 1

HCID 178508208HCID 178508208, compoundYield 40.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8003PentaneSolvent

Procedure

To a solution of 250 mg of 2-[(tert-butoxycarbonyl)amino]-1H-benzimidazol-5-yl 2,6-dichlorobenzenesulfonate in 20 cm3 of dichloromethane are added 746 mg of trifluoroacetic acid. After stirring overnight at a temperature in the region of 20° C., 746 mg of trifluoroacetic acid are added. After stirring for 24 hours, the reaction medium is concentrated to dryness under reduced pressure (2 kPa) and then taken up in 40 cm3 of saturated aqueous sodium hydrogen carbonate solution. The aqueous phase is extracted with five times 60 cm3 of dichloromethane and the combined organic phases are dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure (2 kPa). After flash chromatography on a column of silica [eluent: dichloromethane/methanol (90/10 by volume)], the resin obtained is solidified in 5 cm3 of pentane and the solid obtained is filtered off by suction and then washed with three times 2 cm3 of pentane and dried under reduced pressure over phosphorus pentoxide. 80 mg of 2-amino-1H-benzimidazol-5-yl 2,6-dichlorobenzenesulfonate are obtained in the form of a beige-coloured powder, the characteristics of which are as follows:

Workup

  1. additionare added
  2. concentrationthe reaction medium is concentrated to dryness under reduced pressure (2 kPa)
  3. extractionThe aqueous phase is extracted with five times 60 cm3 of dichloromethane
  4. dry with materialthe combined organic phases are dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure (2 kPa)
  7. customAfter flash chromatography on a column of silica [eluent: dichloromethane/methanol (90/10 by volume)], the resin obtained
  8. customthe solid obtained
  9. filtrationis filtered off by suction
  10. washwashed with three times 2 cm3 of pentane
  11. dry with materialdried under reduced pressure over phosphorus pentoxide

Sources & evidence

ORD record
ord-c91d7496ac81417294e10d318622b99b
Source dataset
uspto-grants-2012_02
Patent number
US08110571B2

Reaction notes

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