Iodine → HCID 71548691, compound

HRID 1526518Notes

Reaction equation

HRID 1526518 reaction equation
II.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.[CH2:29]([C@:36]1([C:51]([NH:53][CH:54]([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[CH:55]=O)=[O:52])[O:40][C:39](=[O:41])[N:38]([C@@H:42]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH3:43])[C:37]1=[O:50])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(=O)([O-])O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[CH2:29]([C@:36]1([C:51]2[O:52][CH:55]=[C:54]([C:57]3[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=3)[N:53]=2)[O:40][C:39](=[O:41])[N:38]([C@@H:42]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH3:43])[C:37]1=[O:50])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

8

Reactant 6

HCID 807IodineHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 24477Sodium ThiosulfateHCID 516892Sodium BicarbonateHCID 90407219HCID 90407219, compound

Product 1

HCID 71548691HCID 71548691, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To iodine (111 mg, 0.438 mmol) in dichloromethane (2 mL) was added triphenylphosphine (121 mg, 0.46 mmol). After 5 min triethylamine (0.122 mL, 0.876 mmol) was added. After 5 min a solution of the product from Step B (100 mg, 0.219 mmol) in dichloromethane (2 mL) was added. After stirring at ambient temperature for 1 h, a 1:1 mixture of saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium thiosulfate (5 mL) was added. The biphasic mixture was stirred for 10 min, the layers were separated and the aqueous phase extracted with dichloromethane (3×5 mL). The combined organic phases were washed with saturated aqueous brine (1×5 mL), dried with anhydrous sodium sulfate, filtered and the solvent removed in vacuo. The yellow oil was purified by reverse phase HPLC(YMC Pro-C 18 column, gradient elution, 20% to 100% acetonitrile/water with 0.1% TFA) to afford the title compound as a colorless amorphous solid. LC/MS 439.1 (M+1). IC50 value=C rating.

Workup

  1. additionwas added
  2. stirringThe biphasic mixture was stirred for 10 min
  3. customthe layers were separated
  4. extractionthe aqueous phase extracted with dichloromethane (3×5 mL)
  5. washThe combined organic phases were washed with saturated aqueous brine (1×5 mL)
  6. dry with materialdried with anhydrous sodium sulfate
  7. filtrationfiltered
  8. customthe solvent removed in vacuo
  9. customThe yellow oil was purified by reverse phase HPLC(YMC Pro-C 18 column, gradient elution, 20% to 100% acetonitrile/water with 0.1% TFA)

Sources & evidence

ORD record
ord-e950a75997c0458aa6cd5af96cf78442
Source dataset
uspto-grants-2015_07
Patent number
US09085568B2

Reaction notes

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