Iodine → HCID 57826352, compound

HRID 1665856Notes

Reaction equation

HRID 1665856 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.II.C(N(CC)CC)C.[CH3:29][O:30][C:31](=[O:58])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][C:38](=[O:57])[NH:39][CH:40]([C:51]1[CH:56]=[CH:55][N:54]=[CH:53][CH:52]=1)[C:41]([C:43]1[CH:48]=[CH:47][C:46]([O:49][CH3:50])=[CH:45][CH:44]=1)=O>C(Cl)Cl.C(OCC)(=O)C.O>[CH3:29][O:30][C:31](=[O:58])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][C:38]1[O:57][C:41]([C:43]2[CH:48]=[CH:47][C:46]([O:49][CH3:50])=[CH:45][CH:44]=2)=[C:40]([C:51]2[CH:56]=[CH:55][N:54]=[CH:53][CH:52]=2)[N:39]=1

Participants

8

Reactant 4

HCID 807IodineHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 57826346HCID 57826346, compound

Product 1

HCID 57826352HCID 57826352, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Triphenyl phosphine (278 mg, 1.06 mmol), iodine (269 mg, 1.06 mmol) and triethylamine (0.3 mL, 2.12 mmol) were added at 0° C. to a solution in which 7-[2-(4-methoxy-phenyl)-2-oxo-1-pyridin-4-yl-ethylcarbamoyl]-heptanoic acid methyl ester (218 mg, 0.53 mmol) prepared in Step 5 was dissolved in 1.5 mL of methylene chloride, and the resulting mixture was stirred for 30 min. The reaction materials were elevated to room temperature and were further stirred for 1 day. After the reaction was complete, the reaction materials were diluted with 50 mL of ethyl acetate and 50 mL of water to dissolve salts, followed by separation of layers. The obtained organic layer was successively washed twice with 50 mL of a brine solution. The organic layer was dried over magnesium sulfate, filtered, concentrated under reduced pressure and purified by silica gel column chromatography to afford 7-[5-(4-methoxy-phenyl)-4-pyridin-4-yl-oxazol-2-yl)-heptanoic acid methyl ester of the following formula.

Workup

  1. customwere elevated to room temperature
  2. stirringwere further stirred for 1 day
  3. dissolutionto dissolve salts
  4. customfollowed by separation of layers
  5. washThe obtained organic layer was successively washed twice with 50 mL of a brine solution
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-6d573fe29a234df3b95a04b4040f4daa
Source dataset
uspto-grants-2011_10
Patent number
US08039634B2

Reaction notes

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