Iodine → HCID 68175843, compound

HRID 1477836Notes

Reaction equation

HRID 1477836 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]([N:45]2[C:53]3[C:48](=[C:49]([NH:54][C:55](=[O:61])[O:56][C:57]([CH3:60])([CH3:59])[CH3:58])[CH:50]=[CH:51][CH:52]=3)[CH:47]=[CH:46]2)([CH2:43][CH3:44])[C:31]([NH:33][CH:34]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH2:35][OH:36])=O)=[CH:26][CH:25]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.II>C(Cl)Cl>[Cl:23][C:24]1[CH:25]=[CH:26][C:27]([C:30]([N:45]2[C:53]3[C:48](=[C:49]([NH:54][C:55](=[O:61])[O:56][C:57]([CH3:58])([CH3:60])[CH3:59])[CH:50]=[CH:51][CH:52]=3)[CH:47]=[CH:46]2)([C:31]2[O:36][CH:35]=[C:34]([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)[N:33]=2)[CH2:43][CH3:44])=[CH:28][CH:29]=1

Participants

7

Reactant 5

HCID 807IodineHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 159087TriacetoxyperiodinaneHCID 68175842HCID 68175842, compound

Product 1

HCID 68175843HCID 68175843, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Dess-Martin periodinane (46 mg, 0.109 mmol) was added to a stirred solution of 9b (40 mg, 0.073 mmol) in DCM (0.73 mL) at 0° C. After 2 h, the reaction was quenched by addition of saturated aqueous sodium thiosulfate and extracted with DCM. The combined organics were washed with water and brine, dried (Na2SO4), filtered and concentrated in vacuo to afford crude residue that was dissolved in DCM (1 mL) and added dropwise to a stirred solution in which triphenylphosphine (172 mg, 0.657 mmol), followed by triethylamine (31 μL, 0.220 mmol), had been added to iodine (28 mg, 0.110 mmol) in DCM (1 mL) at 0° C. The resulting mixture was warmed to rt, and after 1 h, quenched with saturated aqueous sodium thiosulfate. The mixture was extracted with ethyl acetate, and the combined organics were washed with water and brine, dried (Na2SO4), filtered and concentrated in vacuo to afford crude residue that was purified by flash chromatography on silica gel (gradient elution; 0%-50% EtOAc/hexanes as eluent) to afford the title compound 9c. m/z (ES) 528 (MH)+.

Workup

  1. customthe reaction was quenched by addition of saturated aqueous sodium thiosulfate
  2. extractionextracted with DCM
  3. washThe combined organics were washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto afford crude residue that
  8. waitafter 1 h
  9. customquenched with saturated aqueous sodium thiosulfate
  10. extractionThe mixture was extracted with ethyl acetate
  11. washthe combined organics were washed with water and brine
  12. dry with materialdried (Na2SO4)
  13. filtrationfiltered
  14. concentrationconcentrated in vacuo
  15. customto afford crude residue that
  16. customwas purified by flash chromatography on silica gel (gradient elution; 0%-50% EtOAc/hexanes as eluent)

Sources & evidence

ORD record
ord-16d4720caf2242d4a128ffafcccc1a06
Source dataset
uspto-grants-2016_08
Patent number
US09403807B2

Reaction notes

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