Trifluoroacetic acid → HCID 58399742, compound

HRID 1897840Notes

Reaction equation

HRID 1897840 reaction equation
C(OC([NH:8][C:9]1[C:13]([NH:14]C(OC(C)(C)C)=O)=[CH:12][S:11][C:10]=1[C:22]1[CH:27]=[CH:26][C:25]([C:28]2[S:29][CH:30]=[C:31]([NH:41]C(OC(C)(C)C)=O)[C:32]=2[NH:33]C(=O)OC(C)(C)C)=[CH:24][CH:23]=1)=O)(C)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C>[NH2:33][C:32]1[C:31]([NH2:41])=[CH:30][S:29][C:28]=1[C:25]1[CH:24]=[CH:23][C:22]([C:10]2[S:11][CH:12]=[C:13]([NH2:14])[C:9]=2[NH2:8])=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 67236634HCID 67236634, compound

Product 1

HCID 58399742HCID 58399742, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To the resulting tert-butyl 2-[4-(3,4-bis(tert-butoxycarbonylamino)thien-2-yl)phenyl]-4-tert-butoxycarbonylaminothien-3-ylcarbamate was added 80 equivalents of trifluoroacetic acid, and a reaction was performed at 25° C. for 3 hours. The resulting reaction liquid was dropped slowly to a saturated aqueous sodium carbonate solution to neutralize, thereby stopping the reaction. Ethyl acetate was added to the reaction liquid and stirred, and then the organic layer was taken and the solvent was distilled off, and the residue was purified by silica gel column chromatography using an ethyl acetate/hexane solvent, so that 2-[4-(3,4-diaminothien-2-yl)phenyl]thiophene-3,4-diamine was obtained. The yield based on the charged tert-butyl 2-[4-(3,4-bis(tert-butoxycarbonylamino)thien-2-yl)phenyl]-4-tert-butoxycarbonylaminothien-3-ylcarbamate was 90%.

Workup

  1. customThe resulting reaction liquid
  2. customthe reaction
  3. distillationthe solvent was distilled off
  4. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-fa59dfdbe3df4ebfa96f9873de29ca1b
Source dataset
uspto-grants-2013_08
Patent number
US08519150B2

Reaction notes

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