Trifluoroacetic acid → HCID 58399747, compound

HRID 1897839Notes

Reaction equation

HRID 1897839 reaction equation
[O:1]=[C:2]1[N:6](C(OC(C)(C)C)=O)[C:5]2=[CH:14][S:15][C:16]([C:17]3[S:18][C:19]([C:26]4[S:27][CH:28]=[C:29]5[C:33]=4[NH:32][C:31](=[O:34])[N:30]5C(OC(C)(C)C)=O)=[C:20]4[O:25][CH2:24][CH2:23][O:22][C:21]=34)=[C:4]2[NH:3]1.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C>[O:1]=[C:2]1[NH:6][C:5]2=[CH:14][S:15][C:16]([C:17]3[S:18][C:19]([C:26]4[S:27][CH:28]=[C:29]5[C:33]=4[NH:32][C:31](=[O:34])[NH:30]5)=[C:20]4[O:25][CH2:24][CH2:23][O:22][C:21]=34)=[C:4]2[NH:3]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 67236945HCID 67236945, compound

Product 1

HCID 58399747HCID 58399747, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To the obtained tert-butyl 4-[7-(2,3-dihydro-2-oxo-1-tert-butoxycarbonyl-1H-thieno[3,4-d]imidazol-4-yl)-2,3-dihydrothieno[3,4-b]-1,4-dioxin-5-yl]-2,3-dihydro-2-oxo-1H-thieno[3,4-d]imidazole-1-carboxylate was added 40 equivalents of trifluoroacetic acid, and then 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 an organic layer was taken and the solvent was distilled off. The residue was purified by silica gel column chromatography using an ethyl acetate/hexane solvent, so that 4-[7-(2,3-dihydro-2-oxo-1H-thieno[3,4-d]imidazol-4-yl)-2,3-dihydrothieno[3,4-b]-1,4-dioxin-5-yl]-2,3-dihydro-1H-thieno[3,4-d]imidazol-2-one was obtained. The yield based on the charged tert-butyl 4-[7-(2,3-dihydro-2-oxo-1-tert-butoxycarbonyl-1H-thieno[3,4-d]imidazol-4-yl)-2,3-dihydrothieno[3,4-b]-1,4-dioxin-5-yl]-2,3-dihydro-2-oxo-1H-thieno[3,4-d]imidazole-1-carboxylate 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-134f031973964064a488521f9b608eda
Source dataset
uspto-grants-2013_08
Patent number
US08519150B2

Reaction notes

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