Iodine → HCID 20758621, compound

HRID 23867Notes

Reaction equation

HRID 23867 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:13][C@@H:12]([CH2:23][O:24]CC2C=CC=CC=2)[O:11][C@H:10]1[N:32]1[C:44]2[C:43]3[NH:45][C:46]4[CH:47]=[C:48]([F:53])[C:49]([F:52])=[CH:50][C:51]=4[C:42]=3[C:41]3[C:54](=[O:58])[NH:55][C:56](=[O:57])[C:40]=3[C:39]=2[C:38]2[C:33]1=[CH:34][C:35]([F:60])=[C:36]([F:59])[CH:37]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.II>C(OC(=O)C)(=O)C.C(OCC)(=O)C>[CH2:1]([O:8][C@@H:9]1[C@@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:13][C@@H:12]([CH2:23][OH:24])[O:11][C@H:10]1[N:32]1[C:44]2[C:43]3[NH:45][C:46]4[CH:47]=[C:48]([F:53])[C:49]([F:52])=[CH:50][C:51]=4[C:42]=3[C:41]3[C:54](=[O:58])[NH:55][C:56](=[O:57])[C:40]=3[C:39]=2[C:38]2[C:33]1=[CH:34][C:35]([F:60])=[C:36]([F:59])[CH:37]=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 807IodineHCID 69963592HCID 69963592, compound

Product 1

HCID 20758621HCID 20758621, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 7918Acetic AnhydrideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 12-[4-deoxy-2,3,6-tri-O-benzyl-β-D-glucopyranosyl]-2,3,9,10-tetrafluoro-12,13-dihydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione (6.49 g, 7.97 mmol) in 90 mL of acetic anhydride was added solid I2 (0.406 g, 1.6 mmol) and the mixture was stirred at room temperature for 16 h. The resulting mixture was diluted with ethyl acetate, washed (30% aq. Na2S2O3, saturated aq. NaHCO3, H2O, brine) dried (MgSO4) and evaporated. The residue was taken up in methanol (150 mL), 15 mL of concentrated NH4OH was added and the mixture was stirred at room temperature for 18 h. The mixture was then evaporated to dryness and the residue was chromatographed (SiO2/hexane-ethyl acetate, 95:5 to 1:1) to give 12-[4-deoxy-2,3,-di-O-benzyl-β-D-glucopyranosyl]-2,3,9,10-tetrafluoro-12,13-dihydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione (2.35 g, 41%) and then 12-[4 deoxy-2-O-benzyl-β-D-glucopyranosyl]-2,3,9,10-tetrafluoro-12,13-dihydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione (2.40 g, 48%), both as yellow solids.

Workup

  1. washwashed (30% aq. Na2S2O3, saturated aq. NaHCO3, H2O, brine)
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. addition15 mL of concentrated NH4OH was added
  5. stirringthe mixture was stirred at room temperature for 18 h
  6. customThe mixture was then evaporated to dryness
  7. customthe residue was chromatographed (SiO2/hexane-ethyl acetate, 95:5 to 1:1)

Sources & evidence

ORD record
ord-146b908f201f47feabb7e011d4f4287f
Source dataset
uspto-grants-2005_02
Patent number
US06855698B2

Reaction notes

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